～ところに・ところへ・ところで・ところを

About

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  Usage ①: ～ている・た・ていた + ところに・ところへ
  Used to indicate that an action happens in the middle of, and interrupts another

  Pattern: 「(Action 1)ところに・へ(Action 2)」, where "Action 2" interrupts "Action 1"

E.g. 友達ともだちを待まっているところに、店員てんいんが注文ちゅうもんを取とりにきた。 "The staff came to take my order while I was waiting for my friend."

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  Usage ②: ～ている・た・ていた + ところで
  Used to indicate that a second action follows a preceding action

  Pattern: 「(Action 1)ところで(Action 2)」, where "Action 2" follows completion of "Action 1"

E.g. 最後さいごの一問いちもんを解といたところでちょうどチャイムが鳴なった。 "I just finished the final question when the bell rang."

Note: ～ところ(に・へ・で) has a literary tone and is most commonly used in written contexts.

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  Usage ③: ～ている・た・ていた + ところを
  Used to indicate that a subject is directly affected by a second action, while performing the first

  Pattern: 「(Action1)ところを(Action 2)」, where "Action 2" acts upon the subject performing "Action 1"

E.g. こっそりお菓子かしを食たべているところを見みられてしまった。 "I was seen sneakily eating some snacks."

Summary

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  (～ていた・ている・た form verb)ところ(に・へ) can be used to indicate that an action interrupts, or happens in the middle of another

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  (～た form verb)ところで can be used to indicate that an action happens just when another was completed

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  (～ていた・ている・た form verb)ところを is used to express that the subject of a sentence is directly acted upon by a second action, while performing another

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  ～ところを may be used in literary contexts, or in polite spoken scenarios