Lithium Chloride → (2S,3S)-2-benzyloxy-5-(2-(methylthio)phenyl)pentan-3-ol

HRID 1072053노트

반응식

HRID 1072053 반응식
[Mg:1].Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH3:11].[Cl-:12].[Li+].[CH2:14]([O:21][C@@H:22]([CH3:26])[CH:23]1[O:25][CH2:24]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOCC.C1COCC1.[Cu](Cl)Cl.C(Cl)Cl>[CH3:11][S:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][Mg:1][Cl:12].[CH2:14]([O:21][C@H:22]([C@@H:23]([OH:25])[CH2:24][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH3:11])[CH3:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

10

반응물 4

HCID 433294Lithium ChlorideHCID 5462224MagnesiumHCID 124145821-(Chloromethyl)-2-(methylsulfanyl)benzeneHCID 57223577(3S)-3-benzyloxy-1,2-epoxybutane

생성물 2

HCID 69678578(2S,3S)-2-benzyloxy-5-(2-(methylthio)phenyl)pentan-3-ol수율 229.1%HCID 178503137HCID 178503137, 화합물

시약·촉매·용매 4

HCID 24014Cupric Chloride촉매HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

2-Methylthiophenylmethylmagnesium chloride was prepared from magnesium turnings (654 mg) and 2-(chloromethyl)thioanisole (1.55 g) in ether (29 ml) by the method of J. Am. Chem. Soc. (1943) 65, 295. A solution of lithium chloride (38 mg) and copper(II) chloride (60 mg) in THF (2.8 ml) was added dropwise to the ethereal solution of the Grignard reagent followed by addition of a solution of (2RS,3S)-3-(benzyloxy)-1,2-epoxybutane (0.8 g) in ether (8 ml) below −60° C. The mixture was stirred at −70° C. for 1 h, and then allowed to warm to room temperature and stirred overnight. After cooling, the mixture was quenched with saturated aqueous ammonium chloride solution (22 ml). The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. Column chromatography (CH2Cl2) over silica gel gave a pale brown oil of (2S,3S)-2-benzyloxy-5-(2-(methylthio)phenyl)pentan-3-ol (0.65 g, 45.8%).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. temperatureAfter cooling
  4. customthe mixture was quenched with saturated aqueous ammonium chloride solution (22 ml)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give an oil

출처 및 근거

ORD 기록
ord-5bf87a5e41004f17acc5053d5743f43f
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908940B2

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