Sodium hydride → 1-(4-Formylphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

HRID 2414301ノート

反応式

HRID 2414301 の反応式
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[H-].[Na+].F[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1>CN(C=O)C>[CH:29]([C:28]1[CH:31]=[CH:32][C:25]([O:1][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[CH:5]=[CH:4][C:3]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:26][CH:27]=1)=[O:30]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 129722081-Hydroxy-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

生成物 1

HCID 120741741-(4-Formylphenoxy)-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A solution was prepared of 9.8 g (35 mmol) of 1-hydroxy-2-(3-methoxyphenyl)-6-methoxynaphthalene in 490 mL of DMF under a nitrogen atmosphere and to this solution was slowly added 1.47 g (36.8 mmol) of 60% NaH in mineral oil. After ten minutes, 7.5 mL (70 mmol) of 4-fluorobenzaldehyde was added and the reaction mixture was heated to 70° C. for sixty-four hours. The reaction mixture was evaporated to dryness and the residue partitioned between water and EtOAc. The EtOAc layer was dried with Na2SO4 and chromatographed on a silica gel column eluted with EtOAc-hexane (1:9)(v/v). The final product was further purified by crystallization from MeOH. This yielded 2.4 g of the title compound as a tan solid, mp 145-146° C.

後処理

  1. waitAfter ten minutes
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue partitioned between water and EtOAc
  4. dry with materialThe EtOAc layer was dried with Na2SO4
  5. customchromatographed on a silica gel column
  6. washeluted with EtOAc-hexane (1:9)(v/v)
  7. customThe final product was further purified by crystallization from MeOH

出典と根拠

ORDレコード
ord-235c5b4a460442f5809204c552a2c8b4
出典データセット
uspto-grants-2004_11
特許番号
US06812244B2

反応ノート

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