Cesium carbonate → HCID 22345523, compound

HRID 1700947Notes

Reaction equation

HRID 1700947 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Br[C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[Si:12]([O:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][C:30]([CH3:36])([CH3:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:7][CH:6]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 22345525HCID 22345525, compound

Product 1

HCID 22345523HCID 22345523, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-(4-hydroxyphenyl)-1-(tert-butyldiphenylsilyloxy)propane (5.00 g, 12.8 mmol and methyl 2-bromo-2-methylpropionate (4.53 g, 25.0 mmol in dry acetonitrile (25 ml) was treated with cesium carbonate (8.3 g, 25.4 mmol and the resulting mixture was heated at 60° C. for 3.5 h. The cooled mixture was diluted with ethyl acetate, washed with water, brine and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene) gave 5.88 g (93%) of the title material as a clear oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (magnesium sulfate)
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene)

Sources & evidence

ORD record
ord-1edfaa0660a047689c6bfca3efbc5ebf
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

Loading…