Boron trifluoride → 5-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran

HRID 1376989ノート

反応式

HRID 1376989 の反応式
B(F)(F)F.[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:12]([OH:19])=[C:11]([CH:20](O)[CH:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6].C(=O)([O-])O.[Na+]>ClCCl>[C:5]([O:8][C:9]1[C:14]([C:15]([CH3:17])([CH3:16])[CH3:18])=[CH:13][C:12]2[O:19][C:21]([CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:20][C:11]=2[C:10]=1[C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:7])[CH3:6]

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 11070377HCID 11070377、化合物

生成物 1

HCID 111128205-Acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

BF3 etherate (4.7 ml) was added dropwise to a solution of 4-acetoxy-3,5-di-tert-butyl-2-(2,2-diisoamyl-1-hydroxyethyl)-phenol (17.0 g) in dichloromethane (200 ml) under cooling with ice under a nitrogen atmosphere. After stirring the mixture overnight at room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added. After separating the organic layer, the aqueous layer was subjected to extraction with dichloromethane. The extract was combined with the organic layer, washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off to afford 5-acetoxy-2,2-diisoamyl-4,6-di-tert-butyl-2,3-dihydrobenzofuran [15.5 g (yield, 95%)] as a colorless oil.

後処理

  1. temperatureunder cooling with ice under a nitrogen atmosphere
  2. customAfter separating the organic layer
  3. extractionthe aqueous layer was subjected to extraction with dichloromethane
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-c8c3e030f38c4f29b531e98b292938f9
出典データセット
uspto-grants-1997_09
特許番号
US05663373

反応ノート

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