Imidazole → HCID 10991787、化合物

HRID 60764ノート

反応式

HRID 60764 の反応式
[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

参加物

5

反応物 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10176122(S)-(-)-5-Hydroxymethyl-2(5H)-furanone2 回

生成物 1

HCID 10991787HCID 10991787、化合物収率 81.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6d003c75252749dea05fc17160195613
出典データセット
uspto-grants-2016_09
特許番号
US09441008B2

反応ノート

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