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I know this sentence is correct.
He was too busy working at a factory.

but I wonder whether this sentence is correct and natural. (specially in grammar)
He was too busy to work at a factory.

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21

Both sentences are grammatical, but mean different things.

He was too busy working at a factory.

means that because he was working at a factory so much, he could not do anything else.

He was too busy to work at a factory.

means that because he was doing something else so much, he could not work at a factory.

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    To expand, one might say "He was too busy working at the factory to notice that his wife was cheating on him every afternoon". So with that sentence, he is working at the factory, and that work is precluding him from doing other stuff. The other phrase would be used "Between caring for his toddler, writing a novel, and doing stand-up comedy, he was too busy to work at the factory". So in that case, he's not working at the factory, because other things are precluding him from doing that.
    – swbarnes2
    Oct 3 '14 at 21:30
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Busy + v. + ing

He was too busy working at a factory.

= He was occupied with working at a factory. (he was actually working at a factory)


Too + adj. + to + v.(inf.)

He was too busy to work at a factory.

= He was occupied with doing something else (not working at a factory) that prevented him from working at a factory.

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    To enlarge upon mohamed's correct answer, consider these variations: too thirsty to speak; too heavy to fight in the welterweight division; too short to be a professional basketball player; too weak to be a weightlifter; too preoccupied with texting on his mobile phone to see the trash truck coming down the street; too sore from running the marathon to climb the stairs up to his third-floor apartment. Oct 3 '14 at 16:53
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Perhaps if I point out that 'The colourless green squares rolled speedily up the perpendicular mountain' is wholly correct, it will show how careful you have to be about thinking that a grammatically correct sentence will produce a meaningful statement.

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    That is an interesting illustration, but it doesn't really answer the question.
    – ColleenV
    Oct 5 '14 at 0:07

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