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

HRID 1855038ノート

反応式

HRID 1855038 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5cd1fff663844f70878c094d11e2faca
出典データセット
uspto-grants-2015_02
特許番号
US08962660B2

反応ノート

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