Methanol → 6-Ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman

HRID 1765724Notes

Reaction equation

HRID 1765724 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10](C#C[Si](C)(C)C)[CH:11]=1)[O:8][C:7]([CH3:19])([CH3:18])[CH2:6][C:5]2([CH3:21])[CH3:20].[C:22](=[O:25])([O-])[O-].[K+].[K+].[CH3:28]O>>[C:11]([C:2]1[CH:3]=[C:4]2[C:9](=[C:22]([OH:25])[CH:28]=1)[O:8][C:7]([CH3:18])([CH3:19])[CH2:6][C:5]2([CH3:20])[CH3:21])#[CH:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 574242166-Bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman2×

Product 1

HCID 211072286-Ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman

Conditions

Temperature
80 °C

Procedure

A solution of 6-bromo-8-trimethylsilanylethynyl-2,2,4,4-tetramethyl chroman (Intermediate 18, 0.47 g, 1.56 mmol) in methanol (5 mL) was treated with potassium carbonate (0.2 g, 1.45 mmol) and the resulting reaction mixture was heated at 80° C. for 3 h. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-43f7f5d27c544b728939541501aaae8a
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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