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

HRID 1869854Notes

Reaction equation

HRID 1869854 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-chromanYield 99%

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. The organic phase dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a brown oil (0.35 g, 99%).

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
  5. dry with materialThe organic phase dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e7db1e7687e4ba0ac971aa9e3879ed9
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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