Sodium hydride → 2-[3-(Quinolin-2-ylmethoxy)-benzyloxy]-6-trifluoromethyl-benzaldehyde

HRID 892177Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=1.[H-].[Na+].F[C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:25]=1[CH:26]=[O:27]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[CH2:19][O:20][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:35])[F:34])[C:25]=1[CH:26]=[O:27]

Participants

Conditions

Temperature: 90 °C

Procedure

[3-(Quinolin-2-ylmethoxy)-phenyl]-methanol (300 mg, 1.13 mmol, example 48) is dissolved in DMF (6 mL) and sodium hydride (60%, 60 mg, 1.5 mmol) is added and allowed to stir 20 min. 2-Fluoro-6-(trifluoromethyl)benzaldehyde (0.30 mL, 2.2 mmol) is added and the reaction is heated at 90° C. for 5 h. The reaction is partitioned between ethyl acetate (200 mL) and water (200 mL), dried over magnesium sulfate, filtered, concentrated in vacuo and purified by column chromatography (silica, 25% ethyl acetate in hexanes) to provide the title compound; MS (ESI) 438 (M+H)+.

Workup

customThe reaction is partitioned between ethyl acetate (200 mL) and water (200 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by column chromatography (silica, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-9e609fead1a744eba16d506ba04f7f74
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

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