Imidazole → HCID 54020968, compound

HRID 1978319Notes

Reaction equation

HRID 1978319 reaction equation
[CH3:1][C:2]1([CH3:15])[O:8][CH2:7][C:6]2[CH:9]=[C:10]([CH2:13][OH:14])[CH:11]=[CH:12][C:5]=2[CH2:4][O:3]1.N1C=CN=C1.[C:21]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O.O>[C:21]([Si:25]([O:14][CH2:13][C:10]1[CH:11]=[CH:12][C:5]2[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:8][CH2:7][C:6]=2[CH:9]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 21993607HCID 21993607, compound

Product 1

HCID 54020968HCID 54020968, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.227 g (15.495 mM) of (7,7-dimethyl-5,9-dihydro-6,8-dioxabenzocyclohepten-2-yl)-methanol and 1.27 g (18.6 mM) of imidazole in 20 ml of N,N-dimethylformamide was added 4.69 g (17.0 mM) of tert-butylchlorodiphenylsilane at room temperature and the mixture was stirred for 2 hours. This reaction mixture was poured in water and extracted with 3 portions of diethyl ether. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1) to provide the title compound.

Workup

  1. extractionextracted with 3 portions of diethyl ether
  2. dry with materialThe pooled organic layer was dried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-5190fe5929a14b69a4495a845fd629d9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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