Imidazole → (S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone

HRID 1700955

반응식

HRID 1700955 반응식
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][C@H:15]1[CH2:19][CH2:18][O:17][C:16]1=[O:20]>CN(C)C=O>[Si:6]([O:14][C@H:15]1[CH2:19][CH2:18][O:17][C:16]1=[O:20])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3578532-Hydroxy-gamma-butyrolactone, (2S)-

생성물 1

HCID 10965951(S)-2-(tert-Butyldimethylsilyloxy)-g-butyrolactone수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Imidazole (241 mg, 3.54 mmol, 2.2 equiv) and tert-butyl-dimethylsilyl chloride (267 mg, 1.77 mmol, 1.1 equiv) are added to a solution of (3S)-dihydro-3-hydroxy-2(3H)-furanone 11 (164 mg, 1.61 mmol) in dimethyl formamide (1.5 ml). The mixture is stirred for 24 h at r.t. Purification of the reaction mixture by flash column chromatography (pentane/diethyl ether 10:1) affords (S)-2-(tert-butyidimethylsilyloxy)-γ-butyrolactone 12 (321 mg, 93%) as a colourless oil. [α]D20=−31.7; [α]54620=−37.4 (c=0.86, CHCl3); 13C-NMR (100 MHz, CDCL3): δ(ppm)=175.8; 68.2; 64.7; 32.3; 25.6; 18.2; −4.8; −5.3

후처리

  1. customPurification of the reaction mixture by flash column chromatography (pentane/diethyl ether 10:1)

출처 및 근거

ORD 기록
ord-96752ca5d03c444ba428aedcb2ff3785
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350878B1

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