Aluminium lithium hydride → 2-(4-(2-(6-Methoxy-2,3-dihydrobenzofuran-2-yl)ethyl)phenoxy)ethanol

HRID 2046068노트

반응식

HRID 2046068 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:32]=[CH:31][C:12]2[CH2:13][CH:14]([CH2:16][CH2:17][C:18]3[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24](OCC)=[O:25])=[CH:20][CH:19]=3)[O:15][C:11]=2[CH:10]=1>CCOCC>[CH3:7][O:8][C:9]1[CH:32]=[CH:31][C:12]2[CH2:13][CH:14]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:22][CH2:23][CH2:24][OH:25])=[CH:29][CH:30]=3)[O:15][C:11]=2[CH:10]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 66614916Ethyl 2-(4-(2-(6-methoxy-2,3-dihydrobenzofuran-2-yl)ethyl)phenoxy)acetate

생성물 1

HCID 461995202-(4-(2-(6-Methoxy-2,3-dihydrobenzofuran-2-yl)ethyl)phenoxy)ethanol수율 94%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To the stirred slurry of LiAlH4 (0.01 g, 0.026 mmol) in anhydrous Et2O (5 ml) the solution of the product of Step C (0.04 g, 0.11 mmol) in anhydrous Et2O (2 ml) was added drop wise and stirring was continued for 0.5 h at room temperature. The reaction mixture was quenched with EtOAc: H2O: MeOH mixture (7 ml: 3 ml: 1 ml), diluted to 20 ml with EtOAc and filtered through Celite. The filtrate was evaporated under reduced pressure and dried in vacuo to give the title compound (0.032 g, 94%), as colourless solid. 1H-NMR (CDCl3) 7.13 (d, 2H, J=8.54 Hz); 6.99 (d, 1H, J=8.56 Hz); 6.84 (d, 2H, J=8.58 Hz); 6.38-6.34 (m, 2H); 4.79-4.74 (m, 1H); 4.65 (t, 2H, J=4.14 Hz); 3.96-3.90 (m, 2H); 3.75 (s, 3H); 3.22-3.14 (m, 1H); 2.82-2.68 (m, 2H); 2.11-1.91 (m, 3H).

후처리

  1. customThe reaction mixture was quenched with EtOAc
  2. additionH2O: MeOH mixture (7 ml: 3 ml: 1 ml), diluted to 20 ml with EtOAc
  3. filtrationfiltered through Celite
  4. customThe filtrate was evaporated under reduced pressure
  5. customdried in vacuo

출처 및 근거

ORD 기록
ord-0c9c6be018434dd881f982a81dadf45b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592399B2

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