Lithium Hydroxide → (7E)-8-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-6-[2-(4-cyanophenyl)ethyl]oct-7-enoic acid

HRID 1672704Notes

Reaction equation

[C:1]([C:5]1[CH:40]=[CH:39][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[CH:40]=[CH:39][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 798 mg (1.48 mmol) of ethyl 7E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-[2-(4-cyanophenyl)ethyl]oct-7-enoate in 20 ml of THF and 20 ml of water is mixed with 71 mg (2.97 mmol) of lithium hydroxide and stirred at 50° C. for 12 hours. Cooling is followed by dilution with water and diethyl ether and separation of the phases. The aqueous phase is acidified with 1 M hydrochloric acid and extracted with diethyl ether. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated. 700 mg (1.4 mmol, 93% of theory) of the title compound are obtained.

Workup

temperatureCooling
customis followed by dilution with water and diethyl ether and separation of the phases
extractionextracted with diethyl ether
washThe organic phase is washed with saturated sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-4552b927af7848fdbf0513a2172c4c50
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998988B2

Reaction notes

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