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

HRID 36131ノート

反応式

HRID 36131 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-572d8cf721094a69b86879288ca85f87
出典データセット
uspto-grants-1995_05
特許番号
US05412144

反応ノート

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