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

HRID 1198221ノート

反応式

HRID 1198221 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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-(4benzyloxyphenyl)oxirane.

後処理

  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

出典と根拠

ORDレコード
ord-ce733a4c378049d7a6c08ae58614c9d1
出典データセット
uspto-grants-1994_01
特許番号
US05280032

反応ノート

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