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

HRID 36131Notes

Reaction equation

HRID 36131 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-572d8cf721094a69b86879288ca85f87
Source dataset
uspto-grants-1995_05
Patent number
US05412144

Reaction notes

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