Imidazole → HCID 10991787, 화합물

HRID 60764노트

반응식

HRID 60764 반응식
[OH:1][CH2:2][C@@H:3]1[CH:7]=[CH:6][C:5](=[O:8])[O:4]1.N1C=CN=C1.[C:14]([Si:18](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:18]([O:1][CH2:2][C@@H:3]1[CH:7]=[CH:6][C:5](=[O:8])[O:4]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10176122(S)-(-)-5-Hydroxymethyl-2(5H)-furanone2회

생성물 1

HCID 10991787HCID 10991787, 화합물수율 81.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2.25 g of (25)-2-(hydroxymethyl)-2H-furan-5-one (compound 40b, 2.11 g, 16.0 mmol) and imidazole (1.63 g, 24.0 mmol) in DCM was added tert-butyl(chloro)diphenylsilane (5.2 mL, 20.0 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 hours. The resulting mixture was washed with brine. The aqueous layer was extracted with DCM. The organic layers were combined, washed with 1N hydrochloric acid, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether) to afford 4.6 g of (25)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2H-furan-5-one (compound 40c) as a white solid. MS obsd. (ESI+) [(M+H)+]: 353.

후처리

  1. washThe resulting mixture was washed with brine
  2. extractionThe aqueous layer was extracted with DCM
  3. washwashed with 1N hydrochloric acid
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-6d003c75252749dea05fc17160195613
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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