Water → (2S)-2-((1-Naphthalenyloxy)methyl)oxirane

HRID 2288257

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HRID 2288257 반응식
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].[N+](C1C=C(S(O[CH2:27][C@H:28]2[O:30][CH2:29]2)(=O)=O)C=CC=1)([O-])=O.O>CN(C=O)C>[O:30]1[CH2:29][C@H:28]1[CH2:27][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 70051-NaphtholHCID 25953Cesium fluorideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

생성물 1

HCID 148933(2S)-2-((1-Naphthalenyloxy)methyl)oxirane수율 96.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

1-Naphthol (1.0 g) was dissolved in DMF (8 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Cesium fluoride (2.11 g) was added thereto and the mixture was stirred for 1 hour. Then, (S)-glycidyl m-nitrobenzenesulfonate (1.80 g, 99.3% e.e.) was added thereto and the mixture was stirred for 24 hours at the same temperature. After the reaction, water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 6:1) to give 1.34 g of (S)-1-(2,3-epoxypropoxy)naphthalene (yield 96.5%, optical purity 99.2% e.e.) as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 24 hours at the same temperature
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

출처 및 근거

ORD 기록
ord-0b822150599e487ab5c5bf2b5559675d
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06087512

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