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

HRID 1290425
Notes
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Reaction equation

HRID 1290425 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 EtherSolvent
HCID 22350042
dichloromethane N,N-dimethylformamide
Solvent

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-13d57394db864a42a66f853420884d20
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05750735

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes