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

HRID 367302ノート

反応式

HRID 367302 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-03f7986ec16f48638648064430d8027f
出典データセット
uspto-grants-2000_10
特許番号
US06133279

反応ノート

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