Imidazole → 6-(Tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one

HRID 222464

반응식

HRID 222464 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1.N1C=CN=C1.[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Cl)([CH3:20])([CH3:19])[CH3:18]>ClCCl.[Cl-].[Na+].O>[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[CH:3]=1)([CH3:20])([CH3:18])[CH3:19]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2357176-Hydroxy-3-coumaranone

생성물 1

HCID 685261616-(Tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 6-hydroxy-benzofuran-3-one (1.01 g, 6.73 mmol) in dry dichloromethane (18 mL) was added imidazole (0.458 g, 6.727 mmol) followed by tert-butyldiphenylchlorosilane (1.72 mL, 6.73 mmol) at room temperature. The mixture was stirred overnight and poured into brine. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, evaporated in vacuo and the residue was purified by column chromatography (ethylacetate:hexane; 1:9) to give the 6-(tert-butyl-diphenyl-silanyloxy)-benzofuran-3-one as slightly yellow oil (1.34 g, 52%). 1H NMR (CDCl3, 400 MHz) 1.21 (s, 9H), 4.54 (s, 2H), 6.40 (s, 1H), 6.55 (dd, J=1.6, 8.0 Hz, 1H), 7.38-7.50 (m, 7H), 7.67 (m, 4H).

후처리

  1. extractionThe aqueous phase was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated in vacuo
  4. customthe residue was purified by column chromatography (ethylacetate:hexane; 1:9)

출처 및 근거

ORD 기록
ord-6079800153794aac983a1ae9d9c44a76
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207216B2

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