Imidazole → 1-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol

HRID 1450339Notes

Reaction equation

HRID 1450339 reaction equation
[CH2:1]([OH:9])[CH:2]([OH:8])[CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6].N1C=CN=C1.[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl.CN(C)C=O.C(OCC)C>[CH3:31][C:28]([Si:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[O:9][CH2:1][CH:2]([OH:8])[CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 112979875-Hexene-1,2,3-triol

Product 1

HCID 220709881-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diolYield 73%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A 0° C. solution of 7.33 g of product from Example 273 in 120 ml of 5:1 dry methylene chloride/N,N-dimethylformamide is treated with 5.29 g of imidazole and 16.77 g of t-butyl diphenylsilyl chloride. The reaction mixture is warmed to room temperature and stirred vigorously for 16 hours, diluted with diethyl ether and filtered. The filtrate is concentrated and purified by chromatography (Silica Gel: 0-50% ethyl acetate/hexane) to give 15 g of the desired product.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. custompurified by chromatography (Silica Gel: 0-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-53b806a6a0af426b9102a0d8f4eb58fa
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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