Imidazole → 12-(Tert-Butyldimethylsilyloxy)-5,7-dodecadiyn-1-ol

HRID 36131노트

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HRID 36131 반응식
[CH2:1]([OH:14])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].ClCCl>CN(C)C=O>[Si:20]([O:14][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[C:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 5608785,7-Dodecadiyne-1,12-diol

생성물 1

HCID 1994008912-(Tert-Butyldimethylsilyloxy)-5,7-dodecadiyn-1-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5,7-Dodecadiyn-1,12-diol (1) (4 g, 20.6 mmol) and imidazole (2.8 g, 41 mmol) were dissolved in dimethylformamide (15 ml). To the solution, tert-butyldimethylsilylchloride (2.38 g, 18.8 mmol) was added at once. The solution was stirred for 20 hours at room temperature under a nitrogen atmosphere. At this point, the reaction mixture was transferred into a separatory funnel along with dichloromethane (100 ml) and washed with saturated sodium bicarbonate solution and water successively. The organic layer was died (MgSO4) and concentrated followed by purification of the residue by flash column chromatography (silica gel, 7% acetone in dichloromethane) affording 3.17 g of a pale yellow oil (55% yield) of the title compound.

후처리

  1. washwashed with saturated sodium bicarbonate solution and water successively
  2. concentrationconcentrated
  3. customfollowed by purification of the residue by flash column chromatography (silica gel, 7% acetone in dichloromethane)

출처 및 근거

ORD 기록
ord-572d8cf721094a69b86879288ca85f87
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05412144

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