Dimethyl Sulfate → HCID 68936355, compound

HRID 2218776Notes

Reaction equation

HRID 2218776 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[CH:15][CH2:16][OH:17])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[H-].[Na+].S(OC)(O[CH3:26])(=O)=O>>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[CH:15][CH2:16][O:17][CH3:26])[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 68933976HCID 68933976, compound

Product 1

HCID 68936355HCID 68936355, compoundYield 82%

Procedure

Treat 2-(2-chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-ethanol (1 equivalent) with sodium hydride (2 equivalents) in a suitable dry solvent at 0° C. and stir for 15 minutes. Add dimethyl sulfate dropwise (2 equivalents) and stir at 0° C. for one hour. Quench with aqueous citric acid solution and partition between water and ethyl acetate. Dry and evaporate the organic layer. Purify the residue by silica gel chromatography to give the title compound in 82% yield

Workup

  1. customQuench with aqueous citric acid solution
  2. custompartition between water and ethyl acetate
  3. customDry
  4. customevaporate the organic layer
  5. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-57943678e2094650a1b520cce0ce948d
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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