Imidazole → HCID 131718791, compound

HRID 1492019Notes

Reaction equation

HRID 1492019 reaction equation
O[CH:2]1[CH:7]([CH2:8][CH2:9][CH2:10][OH:11])[CH:6]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[O:5][C:3]1=O.N1C=CN=[CH:19]1.[C:23]([Si:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)Cl)([CH3:26])([CH3:25])[CH3:24].[C:41](OCC)(=[O:43])[CH3:42]>>[Si:27]([O:11][CH2:10][CH2:9][CH2:8][C:7]([CH2:2][C:3](=[O:5])[CH3:19])([CH2:6][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH:41]([OH:43])[CH3:42])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 94078tert-ButyldiphenylchlorosilaneHCID 18953757HCID 18953757, compound

Product 1

HCID 131718791HCID 131718791, compound

Procedure

To a solution of 37.23 g (0.157 mol) of the crude 2-hydroxy-3-(3-hydroxy-1-propyl)-4-(3-pyridyl)-γ-butyrolactone in 170 ml of dimethylformide are added 21.4 g (0.157 mol) of imidazole and 23.63 g (0.157 mol) of t-butyldiphenylchlorosilane and the mixture is stirred at room temperature overnight. The mixture is diluted with ethyl acetate and washed with water (2×), brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography from silica gel using ethyl acetate:methylene chloride (1:1) as eluent to give 3-[3-(t-butyldiphenylsilyloxy)-1-propyl]-2-hydroxy-4-(3-pyridyl)-γ-butylactone which crystallizes from ether-petroleum ether and having mp 81°-84° C. and elemental analysis: C, 61,52; H, 8.21; N, 3.91 (theory, C, 61.50; H, 8.32; N, 3.98).

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue is purified by flash chromatography from silica gel

Sources & evidence

ORD record
ord-44bb82525dfb438b96692e24c4e34c98
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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