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

HRID 39201ノート

反応式

HRID 39201 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-50a932390a1349edb38f54c4732c6ca6
出典データセット
uspto-grants-2013_09
特許番号
US08524767B2

反応ノート

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