Ethyl 2,2-dimethylhex-5-enoate → 2,2-Dimethylhex-5-en-1-ol

HRID 1511557ノート

反応式

HRID 1511557 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[C:9](OCC)=[O:10]>CCOCC>[CH3:7][C:8]([CH3:18])([CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:9][OH:10]

参加物

4

反応物 2

HCID 14906730Ethyl 2,2-dimethylhex-5-enoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 102408212,2-Dimethylhex-5-en-1-ol収率 87.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
22 °C

実験手順

To a stirred solution of 1M LAH in ether (142.14 mL, 142.14 mmol), at 0° C. and under nitrogen, was added dropwise ethyl 2,2-dimethylhex-5-enoate (11.00 g, 64.61 mmol) dissolved in 100 mL anhydrous ether over 1 hour. This reaction solution was stirred at 22° C. for 20 hours, then quenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL), dried over Na2SO4, filtered and concentrated to give the title product (7.22 g, 87.09%). 1H NMR (500 MHz, CDCl3) δ 5.85-5.77 (m, 1H); 5.01 (d, 1H); 4.93 (d, 1H); 3.33 (d, 2H); 2.03 (m, 2H); 1.34 (m, 2H); 0.89 (m, 6H) ppm.

後処理

  1. customquenched with water (3 mL), 1M NaOH (11 mL) and water (9 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-aa5c53fba5f14b629e9ca3488e75c42b
出典データセット
uspto-grants-2012_07
特許番号
US08216999B2

反応ノート

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