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Water → HCID 22058567, compound

HRID 1828808
Notes
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Reaction equation

HRID 1828808 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[O:14]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39]OS(C)(=O)=O)=[CH:35][C:34]=1[Cl:45])[Si:15]([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.O>CN(C)C=O>[O:14]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:35][C:34]=1[Cl:45])[Si:15]([C:28]([CH3:29])([CH3:30])[CH3:31])([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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium CarbonateHCID 17818600HCID 17818600, compound

Product 1

HCID 22058567HCID 22058567, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of phenol (969 mg) in N,N-dimethylformamide (27 ml) was added potassium carbonate powder (1.92 g) and the mixture was stirred at room temperature for 5 min. 1-((tert-Butyldiphenylsiloxy)methyl)-2-chloro-4-((methanesulfonyloxy) methyl)benzene (3.39 g) was added and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was allowed to cool to room temperature. Water was added and the mixture was extracted twice with hexane. The organic layers were combined, washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/1) to give 1-((tert-butyldiphenylsiloxy)-methyl)-2-chloro-4-(phenoxymethyl)benzene (2.65 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at 100° C. for 3 hr
  2. temperatureto cool to room temperature
  3. extractionthe mixture was extracted twice with hexane
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-bb5381151d1a4171b2710558642b2107
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07060721B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes