Imidazole → Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

HRID 1160612ノート

反応式

HRID 1160612 の反応式
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C=O)C.CCOC(C)=O>[Si:22]([O:1][CH:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

参加物

7

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14530758Benzyl 3-hydroxycyclopentanecarboxylate

生成物 1

HCID 68717013Benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of benzyl 3-hydroxycyclopentanecarboxylate (1.0 g, 4.54 mmol) in 9 ml of degassed DMF was added imidazole (0.34 g, 4.99 mmol) and tert-butyldimethylsilyl chloride (0.75 g, 4.99 mmol). The mixture was stirred at ambient temperature for 4 hours, and then poured into 70 mL of water, and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with water and brine and then dried over sodium sulfate. Filtration and concentration afforded the crude product which was subjected to chromatography on silica gel eluting with 5% EtOAc in hexanes to give benzyl 3-{[tert-butyl(dimethyl)silyl]oxy}cyclopentanecarboxylate.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration
  5. customafforded the crude product which

出典と根拠

ORDレコード
ord-fe3af9218aee4e8d81d4a254c58e43b1
出典データセット
uspto-grants-2010_10
特許番号
US07816380B2

反応ノート

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