Hydrochloric Acid → 4-[7-(1-Adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzenemethanol

HRID 1976168

Reaction equation

[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.B.Cl>C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:29]=[CH:28][C:24]([CH2:25][OH:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

Conditions

Temperature: 40 °C

Procedure

3 g (6.1 mmol) of 4-[7-(1-adamantyl)-6-methoxyethoxymethoxy-2-naphthyl]benzoic acid and 40 ml of THF were introduced into a three-necked flask under a stream of nitrogen. 20 ml of a solution of borane (1M in THF) were added dropwise and the reaction mixture was heated at 40° C. for one hour. The reaction mixture was poured into a 1N hydrochloric acid solution and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulfate and evaporated.

Workup

extractionextracted with ethyl acetate
customthe organic phase was separated
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-001ebf85415340179869c6543ca861cd
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225328B1

Linked notes

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