Imidazole → HCID 86080037, compound

HRID 748560Notes

Reaction equation

HRID 748560 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][O:6][CH3:7])[CH2:3][OH:4].N1C=CN=C1.C(N(CC)CC)C.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C)C=O.O>[CH3:1][C:2]([CH3:8])([CH2:3][O:4][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:5][O:6][CH3:7]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1434401-Propanol, 3-methoxy-2,2-dimethyl-

Product 1

HCID 86080037HCID 86080037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1 g of 2,2-dimethyl-3-methoxy-1-propanol was admixed with 10 ml of N,N-dimethyl formamide, and 0.29 g of imidazole was added thereto. The mixture was cooled in ice-water bath, and 1.65 ml of triethyl amine was added thereto. After stirring for 5 minutes, 1.65 g of tert-butyldimethylsilyl chloride in 10 ml of N,N-dimethyl formamide was slowly added to the reaction mixture, and the mixture was stirred in ice-water bath for further 4 hours. The reaction mixture was diluted with 10 ml of water, and extracted twice with 20 ml of dichloromethane for each time. The combined dichloromethane extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to dryness to give 1.78 g of concentrate of 2,2-dimethyl-1-methoxy-3-[(tert-butyldimethylsilyl)oxy]-propane. The crude product was purified by column chromatography using petroleum ether as eluent, to give colorless pure compound.

Workup

  1. additionwas added
  2. extractionextracted twice with 20 ml of dichloromethane for each time
  3. extractionThe combined dichloromethane extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate was evaporated to dryness
  7. customto give 1.78 g
  8. concentrationof concentrate of 2,2-dimethyl-1-methoxy-3-[(tert-butyldimethylsilyl)oxy]-propane
  9. customThe crude product was purified by column chromatography
  10. customto give colorless pure compound

Sources & evidence

ORD record
ord-3ffa936e9b0c45b2aa65809ad6dedfdf
Source dataset
uspto-grants-2008_07
Patent number
US07399812B2

Reaction notes

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