Imidazole → HCID 18953760, compound

HRID 1492018Notes

Reaction equation

HRID 1492018 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:24])[CH:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1)[CH2:12][CH2:13][CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[C:30]([Si:34]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)Cl)([CH3:33])([CH3:32])[CH3:31]>CN(C)C=O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH:10]([OH:24])[CH:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1)[CH2:12][CH2:13][CH2:14][O:15][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 18953764HCID 18953764, compound

Product 1

HCID 18953760HCID 18953760, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.69 g (0.0133 mole) of 1-(t-butyldimethylsilyloxy)-3-nicotinoylhexan-2,6-diol, 2.18 g (0.032 mole) of imidazole in 12 ml of dimethylformamide is added at once 4.38 g (0.0159 mole) of t-butyldiphenylchlorosilane, the mixture is stirred at room temperature overnight, diluted with 30 ml of ethyl acetate and washed with water (2×10 ml) and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using ethyl acetate-methylene chloride (2:3) as eluent to give 1-(t-butyldimethylsilyloxy)-6-(t-butyldiphenylsilyloxy)-3-nicotinoylhexan-2-ol as an oil.

Workup

  1. washwashed with water (2×10 ml) and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-661706b608804da7997b87b8a8309edf
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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