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Acetone Cyanohydrin → (3S)-3-hydroxy-3-phenylpropanenitrile

HRID 846341
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HRID 846341 반응식
[CH2:1]1[O:9][C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)(O)[C:12]#[N:13].C(N(CC)CC)C>O1CCCC1>[C:3]1([C@@H:2]([OH:9])[CH2:1][C:12]#[N:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 114705(+)-Styrene oxide

생성물 1

HCID 11084031(3S)-3-hydroxy-3-phenylpropanenitrile수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 40.0 g of (R)-styrene oxide, 31.12 g of acetone cyanohydrin, 36.96 g of triethylamine, and 150 ml of tetrahydrofuran was heated at reflux for 18 hours. The reaction mixture was cooled, concentrated in vacuo, diluted with 200 ml of 2N potassium hydroxide, and extracted with diethyl ether. The ether extracts were combined, dried over magnesium sulfate, and concentrated in vacuo providing 34.3 g of the title intermediate.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with 200 ml of 2N potassium hydroxide
  6. extractionextracted with diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-031d64a9ec0c47989fe335f90f58eb3c
출처 데이터셋
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05136078

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