Imidazole → HCID 67793159, compound

HRID 1741969Notes

Reaction equation

HRID 1741969 reaction equation
[OH:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:3]1[OH:19].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(Cl)Cl.C(OCC)C>[Si:25]([O:1][CH:2]1[CH:7]2[CH2:8][O:9][N:10]=[C:6]2[CH2:5][CH:4]([O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14])[CH:3]1[OH:19])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67793468HCID 67793468, compound

Product 1

HCID 67793159HCID 67793159, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

4,5-Dihydroxy-6-(tert-butyldimethylsilyloxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (287 mg) was dissolved in 10 ml of methylene chloride, and 200 mg of imidazole and 226 mg of tert-butyldimethylsilyl chloride were added under ice cooling, followed by stirring the mixture overnight at room temperature. The reaction mixture was diluted with diethyl ether, washed with dilute hydrochloric acid, a sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 265 mg of 4,6-bis(tert-butyldimethylsilyloxy)-5-hydroxy-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 66%).

Workup

  1. washwashed with dilute hydrochloric acid
  2. concentrationa sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence, and concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d15ab81c8314432bf054a72b8177b24
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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