Diethyl Ether → (2S)-2-[4-(benzyloxy)phenyl]oxirane

HRID 2259340노트

반응식

HRID 2259340 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([OH:18])[CH2:16]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(OCC)C>CO.O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:16][O:18]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 3

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 11716484(S)-1-(4-benzyloxyphenyl)-2-bromoethanol

생성물 1

HCID 22849959(2S)-2-[4-(benzyloxy)phenyl]oxirane수율 67.9%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2.8 g of (S)-1-(4-benzyloxyphenyl)-2-bromoethanol was dissolved in a mixed solvent of 20 ml of methanol and 10 ml of tetrahydrofuran. To the solution was added a solution of 0.8 g of potassium hydroxide dissolved in 4 ml of water, with ice cooling. The mixture was stirred for 5 minutes at the same temperature and further for 10 minutes at room temperature. The reaction mixture was added to a mixture of 50 ml of diethyl ether and 50 ml of ice water. The organic layer was separated. The aqueous layer was extracted with 25 ml of diethyl ether. The extract was combined with the previously separated organic layer. The combined organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.4 g of (S)-2-(4-benzyloxyphenyl)oxirane.

후처리

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with 25 ml of diethyl ether
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-cbc7f78b92274d5db93d015dbb64b3c7
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05472984

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