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

HRID 2414301Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-235c5b4a460442f5809204c552a2c8b4
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812244B2

Reaction notes

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