Aluminium lithium hydride → (5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

HRID 1876402ノート

反応式

HRID 1876402 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:13](OC)=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:13][OH:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 58566735Methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate

生成物 1

HCID 58566787(5-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylate (668) (466 mg, 1.63 mmol) in tetrahydrofuran (16 mL) at 0° C. was added LAH (1 mL, 1.96 mmol). The reaction was stirred at 0° C. for 1 hour and quenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water. The reaction was warmed to room temperature and diluted with diethyl ether. Magnesium sulfate was added and the solution was filtered, washed with diethyl ether, and the solvent removed in vacuo to provide (5-bromo-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)methanol (669).

後処理

  1. customquenched with 0.2 mL of water, 0.2 mL of 15% NaOH and 0.6 mL of water
  2. temperatureThe reaction was warmed to room temperature
  3. additiondiluted with diethyl ether
  4. additionMagnesium sulfate was added
  5. filtrationthe solution was filtered
  6. washwashed with diethyl ether
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-1c6b43d2ddb44ce9a36bd6dd343520e6
出典データセット
uspto-grants-2012_11
特許番号
US08309600B2

反応ノート

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