Dichloromethane → (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol

HRID 1026562노트

반응식

HRID 1026562 반응식
ClCCl.[CH2:4]([OH:9])[CH2:5][C@@H:6]([OH:8])[CH3:7].[C:10]([Si:14](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>C(N(CC)CC)C>[Si:14]([O:9][CH2:4][CH2:5][C@@H:6]([OH:8])[CH3:7])([C:10]([CH3:13])([CH3:12])[CH3:11])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 446973(+)-1,3-Butanediol

생성물 1

HCID 58005224(2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Under ice cooling, to a dichloromethane solution (20.0 ml) of (S)-1,3-butanediol (519 mg) were added triethylamine (1.04 ml) and tert-butylchlorodiphenylsilane (1.63 ml), followed by stirring at room temperature overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol (1.69 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-25728101a12f47a6b6ac19b9099b809e
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729095B2

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