Aluminium lithium hydride → 2-(2-(Allyloxy)ethoxy)ethanol

HRID 452345

반응식

HRID 452345 반응식
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9](OC)=[O:10])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])[CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydride2회HCID 59615972Methyl (2-allyloxy-ethoxy)-acetate

생성물 1

HCID 847772-(2-(Allyloxy)ethoxy)ethanol수율 99.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of ester (8) (9.77 g, 55.1 mmol, 1.0 equiv.) in THF (100 mL) was carefully added one portion of LAH (95%, 1.10 g, 27.5 mmol, 0.5 equiv.) at 0° C. After 30 min, another portion of LAH was carefully added and the reaction was stirred for an additional 30 min. The reaction was then carefully quenched with a Na2SO4-saturated aqueous solution. The resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings) and the filtrate was evaporated under reduced pressure. Purification was achieved by Kugelrohr distillation under reduced pressure and provided 7.99 g (99%) of alcohol (9) as a colorless oil; bp>200° C. (water tap vacuum). Spectroscopic data were consistent with those reported in the literature.26 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.19 (m, 1H), 4.04 (m, 2H), 3.73 (m, 2H), 3.68 (m, 2H), 3.62 (m, 4H), 2.36 (brs, 1H).

후처리

  1. customThe reaction was then carefully quenched with a Na2SO4-saturated aqueous solution
  2. filtrationThe resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings)
  3. customthe filtrate was evaporated under reduced pressure
  4. customPurification
  5. distillationwas achieved by Kugelrohr distillation under reduced pressure

출처 및 근거

ORD 기록
ord-955657a80d85420a9c9e424d3cf9d91c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08491958B2

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