Hydrochloric Acid → (4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

HRID 238596Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:20]=[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=1)=O.Cl>O1CCCC1>[CH2:22]([O:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH:12]=[C:11]([CH2:9][OH:8])[CH:20]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To the slurry of lithium aluminum hydride (1.4 g, 36.9 mmol) in tetrahydrofuran (30 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (5.8 g, 18.7 mmol) in tetrahydrofuran (30 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 1 hour under a nitrogen atmosphere, the resulting mixture was cooled to 0° C. and 1 N hydrochloric acid was added to quench the reaction. The aqueous layer was extracted with diethyl ether (50 mL×4). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (4.9 g, 93%) as a white solid.

Workup

temperaturethe resulting mixture was cooled to 0° C.
customto quench
customthe reaction
extractionThe aqueous layer was extracted with diethyl ether (50 mL×4)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8167e80975974b1295aa0707c9c5ba89
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642629B2

Reaction notes

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