Aluminium lithium hydride → 2-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol

HRID 1855038노트

반응식

HRID 1855038 반응식
[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][C:23](O)=[O:24])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][OH:24])([CH2:18][CH2:19]2)[CH2:16][O:15]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 904093542-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid

생성물 1

HCID 904088772-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetic acid (140 mg, 0.414 mmol) and LAH (0.414 mL, 0.414 mmol) in THF (5 mL) was stirred at 0° C. for 2 h. The reaction was quenched with water (1 mL) dropwise and then stirred at rt for 10 min. The mixture was diluted with EtOAc (5 mL) and filtered. The filtrate was washed with water, dried with MgSO4, filtered, and concentrated in vacuo to afford the title compound (64 mg, 48% yield) as a clear oil. LCMS, [M+Na]+=347.1. 1H NMR (500 MHz, CDCl3) δ 7.29-7.16 (m, 3H), 7.10-6.96 (m, 3H), 6.96-6.87 (m, 2H), 6.76 (ddd, J=8.1, 2.5, 1.0 Hz, 1H), 3.77 (s, 2H), 3.62 (t, J=7.3 Hz, 2H), 2.07-1.88 (m, 4H), 1.73-1.57 (m, 4H), 1.38 (t, J=7.3 Hz, 2H).

후처리

  1. customThe reaction was quenched with water (1 mL) dropwise
  2. stirringstirred at rt for 10 min
  3. additionThe mixture was diluted with EtOAc (5 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5cd1fff663844f70878c094d11e2faca
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962660B2

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