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

HRID 1511557

반응식

HRID 1511557 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 102408212,2-Dimethylhex-5-en-1-ol수율 87.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
22 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-aa5c53fba5f14b629e9ca3488e75c42b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08216999B2

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