Imidazole → HCID 69303498, compound

HRID 748565Notes

Reaction equation

HRID 748565 reaction equation
[CH2:1]([C:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH2:11][O:12][CH3:13])[CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.C(N(CC)CC)C.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34]>CN(C)C=O.O>[CH2:14]([C:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:9][O:10][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH2:11][O:12][CH3:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 69303568HCID 69303568, compound

Product 1

HCID 69303498HCID 69303498, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4.16 Mmol of 2,2-dibenzyl-3-methoxy-1-propanol was dissolved in 10 ml of N,N-dimethyl formamide, and 0.14 g (2.08 mmol) of imidazole was added thereto. The solution was cooled in ice-water bath to below 5° C., and 0.87 ml (6.24 mmol) of triethyl amine was added thereto. After stirring for 5 minutes, 0.88 g (5.82 mmol) 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 2 hours, and at room temperature for further 1 hour. The reaction mixture was diluted with 10 ml of water, and extracted using 30 ml of dichloromethane. The organic layer was separated, wished twice with 20 ml of water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to give 2,2-dibenzyl-1-methoxy-3-[(tert-butyldimethylsilyl)oxy]propane.

Workup

  1. waitat room temperature for further 1 hour
  2. extractionextracted
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3dc7583ac0f6440a9bde1be45c71abe5
Source dataset
uspto-grants-2008_07
Patent number
US07399812B2

Reaction notes

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