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

HRID 2414301노트

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HRID 2414301 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-235c5b4a460442f5809204c552a2c8b4
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06812244B2

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