Ethyl Acetate → 1-Methoxy-2-naphthalenemethanol

HRID 1790294ノート

反応式

HRID 1790294 の反応式
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13](OC)=[O:14].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[OH:14][CH2:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[O:2][CH3:1]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 4640332Methyl 1-methoxy-2-naphthoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 45591511-Methoxy-2-naphthalenemethanol収率 104.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

The product of Step A (4.5 g, 20.83 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to 0° C. To this solution was added a 1 M solution of lithium aluminum hydride in tetrahydrofuran (31 mL). The mixture was stirred at this temperature for 30 min, allowed to warm up to room temperature, and stirred for an additional 30 min. Ethyl acetate (200 mL) was then added carefully to the reaction mixture to destroy the excess of lithium aluminum hydride. The mixture was then diluted with a 1 M solution of aqueous hydrogen chloride (100 mL), the organic layer was separated, dried (MgSO4), and concentrated to give an oil (4.1 g) which solidified: 1H NMR (CDCl3) δ 3.97 (s, 3H, CH3), 4.89 (s, 2H, CH2), 7.51 (m, 3H, Ar—H), 7.60 (m, 1H, Ar—H), 7.82 (m, 1H, Ar—H), 8.07 (m, 1H, Ar—H); MS (GC/MS) 188.

後処理

  1. temperatureto warm up to room temperature
  2. stirringstirred for an additional 30 min
  3. customto destroy the excess of lithium aluminum hydride
  4. additionThe mixture was then diluted with a 1 M solution of aqueous hydrogen chloride (100 mL)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cd5c48fb49a04e97be2dc29a00d259d3
出典データセット
uspto-grants-2006_07
特許番号
US07071225B2

反応ノート

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