Imidazole → HCID 53924315, compound

HRID 1741978Notes

Reaction equation

HRID 1741978 reaction equation
[CH2:1]=[C:2]1[CH:7]([OH:8])[CH:6]([OH:9])[CH:5]([O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].N1C=CN=C1.[Si:39](Cl)([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.O>C(Cl)Cl>[Si:39]([O:8][CH:7]1[CH:6]([OH:9])[CH:5]([O:10][Si:11]([C:24]([CH3:27])([CH3:25])[CH3:26])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][C:3](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:2]1=[CH2:1])([C:52]([CH3:55])([CH3:54])[CH3:53])([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 54296428HCID 54296428, compound

Product 1

HCID 53924315HCID 53924315, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (2-methylene-3,4-dihydroxy-5-(tert-butyldiphenylsilyloxy)cyclohexylidene)acetate (0.466 g) was dissolved in 5 ml of methylene chloride, and 0.204 g of imidazole and 0.30 g of tert-butyldiphenylsilyl chloride were added, followed by stirring the mixture at room temperature for 3 hours. The reaction mixture was poured into water, and extracted with diethyl ether. The extract was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 0.664 g of ethyl (3,5-bis-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-methylene-cyclohexylidene)acetate having the following property.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-238e7df629e54c76980459d53b4bce68
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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