Imidazole → HCID 22598093, compound

HRID 1760256Notes

Reaction equation

HRID 1760256 reaction equation
N1C=CN=C1.[Cl:6][C:7]1[S:11][C:10]([CH:12](O)[CH2:13][OH:14])=[CH:9][CH:8]=1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].CN(C)C=[O:27]>>[Si:16]([O:27][CH:13]([OH:14])[CH2:12][C:10]1[S:11][C:7]([Cl:6])=[CH:8][CH:9]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 22598067HCID 22598067, compound

Product 1

HCID 22598093HCID 22598093, compound

Procedure

Imidazole (0.45 g) was added to a solution of 1(5-chloro-2-thienyl)-1,2-ethanediol (1.0 g, 5.6 mmol) and tert-butyldimethylsilyl chloride (0.80 g) in N,N-dimethylformamide (5 ml) at 5°. The reaction mixture was allowed to come to room temperature and stirred 1 hour, extracted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered, concentrated in vacuo. 1-tert-butyldimethylsilyloxy-2-(5-chloro-2-thienyl)ethan-1-ol (1.14 g) was obtained as a colorless oil after a chromatographic purification. 1,1′-Carbonyldiimidazole (0.95 g) was added to a solution of the foregoing alcohol (1.14 g 3.9 mmol) in dichloromethane (20 mL) at 5°. The reaction mixture was allowed to come to room temperature and stirred 1 hour. Ammonium hydroxide (equivalent to 28% ammonia in water, 10 ml) was added at 5°. The reaction mixture was stirred for 1 hour at room temperature, extracted with ethyl acetate, washed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine. The extracts were dried over sodium sulfate, filtered, concentrated in vacuo. 1-tert-butyldimethylsilyloxy-2-(5-chloro-2-thienyl)-2-carbamoyloxyethane (0.47 g) was obtained as a colorless oil after a chromatographic purification.

Workup

  1. customto come to room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with 0.5N aqueous hydrochloric acid, saturated sodium bicarbonate and brine
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a7c2249ee944a0ba8e26401a83cac88
Source dataset
uspto-grants-2005_01
Patent number
US06841569B2

Reaction notes

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