1,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioate → 2-(4-Bromophenyl)-2-methylpropane-1,3-diol

HRID 640656ノート

反応式

HRID 640656 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:19])([CH2:14][OH:15])[CH2:9][OH:10])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 106163071,3-Diethyl 2-(4-bromophenyl)-2-methylpropanedioateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 124571492-(4-Bromophenyl)-2-methylpropane-1,3-diol収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of diethyl 2-(4-bromophenyl)-2-methylmalonate (850 mg, 2.6 mmol) in dry THF (5 mL) at 0° C. was added a 1.0M solution of lithium aluminum hydride in THF (2.6 mL, 2.6 mmol). After stirring for 2 h at 0° C., the mixture was quenched by slow addition of water (5 mL). The mixture was made acidic by addition of 1N HCl and was then extracted with dichloromethane (2×20 mL). The organics were combined, dried over Na2SO4 and evaporated to give 2-(4-bromophenyl)-2-methylpropane-1,3-diol (500 mg, 79%) 1H NMR (400 MHz, DMSO-d6) δ 7.47-7.43 (m, 2H), 7.35-7.32 (m, 2H), 4.59-4.55 (m, 2H), 3.56-3.51 (m, 4H), 1.17 (s, 3H).

後処理

  1. customthe mixture was quenched by slow addition of water (5 mL)
  2. additionThe mixture was made acidic by addition of 1N HCl
  3. extractionwas then extracted with dichloromethane (2×20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-e9fabb0b936f44b6a0fe2c9c85dfa96f
出典データセット
uspto-grants-2010_04
特許番号
US07691902B2

反応ノート

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