Water → 3-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-

HRID 1842107노트

반응식

HRID 1842107 반응식
[Li][CH2:2]CCC.[I-].C[S+](C)C.[CH2:11]([O:15][C:16](C1C=CC=CC=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:12]1[O:14][CH2:13]1.O.[CH3:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>C1COCC1>[C:16]([O:15][CH2:11][C@@H:12]([OH:14])[CH:13]=[CH2:2])([C:38]1[CH:37]=[CH:36][CH:41]=[CH:40][CH:39]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

7

반응물 5

HCID 962WaterHCID 8058HexaneHCID 75127Trimethylsulfonium iodideHCID 7168113(S)-Glycidyl Trityl EtherHCID 178418339Butyllithium

생성물 1

HCID 114844683-Buten-2-ol, 1-(triphenylmethoxy)-, (2S)-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

A solution of n-BuLi in hexane (2.6 M; 182 mL) was added dropwise to a solution of trimethylsulfonium iodide (96.8 g) in THF (800 mL) at −30° C. After stirring at −20° C. for 20 minutes, (S)-trityl glycidyl ether (50.0 g) was added at the same temperature, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (52.0 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionfollowed by extraction with diethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-08c3ad61c70c487ba350f5414b8474af
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946211B2

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