Tetrabutylammonium Fluoride → 4,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-carboxylic acid

HRID 367302Notes

Reaction equation

HRID 367302 reaction equation
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14]([OH:16])=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[O:22][Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:17])([C:14]([OH:16])=[O:15])[O:13][C:9]=2[CH:8]=[C:7]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=1[OH:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 232880354,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

Product 1

HCID 154857264,6-Di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, a solution of 0.19 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid in 1 ml of THF was cooled to 0° C. and 1 ml of tetra-n-butylammonium fluoride (1.0 mmol/ml THF solution) was added dropwise to this solution and the mixture was stirred for 1 hour. After the reaction was quenched by adding a saturated aqueous ammonium chloride solution, the mixture was extracted with water and diethyl ether, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated to give 0.14 g of 4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-carboxylic acid as a colorless solid (yield 91%).

Workup

  1. customAfter the reaction was quenched
  2. additionby adding a saturated aqueous ammonium chloride solution
  3. extractionthe mixture was extracted with water and diethyl ether
  4. washthe combined organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03f7986ec16f48638648064430d8027f
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

Loading…