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

HRID 1600139Notes

Reaction equation

HRID 1600139 reaction equation
[CH2:1]([OH:9])[CH:2]([OH:8])[CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6].[Si:10](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.CN(C)C=O.C(OCC)C>[CH3:26][C:23]([Si:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[O:9][CH2:1][CH:2]([OH:8])[CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 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 ofimidazole 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-b0b165c4acd148e5b4986166c9eaab4b
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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