Potassium Carbonate → HCID 22345531, compound

HRID 584165Notes

Reaction equation

HRID 584165 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][Sn:23]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[CH2:24]([Sn:23]([CH2:22][O:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[CH:4][CH:3]=1)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:25][CH2:26][CH3:27]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 22345531HCID 22345531, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1,1-dimethylethyl 4-hydroxybenzoate (0.20 g, 1.04 mmol) in N,N-dimethylformamide (4 ml) was treated with powdered anhydrous potassium carbonate (0.4 g) followed by iodomethyltributyltin (0.60 g, 1.4 mmol) [D. E. Seitz, et al, Synth. Commun. (1983) 13, 129-134] and the resulting mixture was stirred at 65° C. for 1 hour. The cooled reaction mixture was diluted with a mixture of hexane and ethyl acetate (9:1), washed with water, brine and dried (magnesium sulfate). Evaporation of the solvent and chromotography of the residue on silica gel (elution hexane-toluene, 1:1) gave 0.494 g (96%) of the title material as an oil.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water, brine
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation of the solvent and chromotography of the residue on silica gel (elution hexane-toluene, 1:1)

Sources & evidence

ORD record
ord-2b3d38b5c8d942f2b8ff1010c416a04d
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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