Carbon Dioxide → 3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid

HRID 1642

Reaction equation

[C:1]12([C:11]3[CH:24]=[C:23](Br)[CH:22]=[CH:21][C:12]=3[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([Li])CCC.[C:31](=[O:33])=[O:32].[Cl-].[NH4+].Cl>O1CCCC1.CCCCCC>[C:1]12([C:11]3[CH:24]=[C:23]([CH:22]=[CH:21][C:12]=3[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C:31]([OH:33])=[O:32])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Conditions

Temperature: -78 °C

Procedure

9.3 g of (2-adamantan-1-yl-4-bromo-phenoxy)-tert-butyl-dimethylsilane were dissolved in 120 ml of absolute tetrahydrofuran and treated dropwise at -78° C. with 15.5 ml of a 1.6 molar solution of n-butyl-lithium in hexane. After stirring at -78° C. for 1.5 hours, a vigorous stream of carbon dioxide was introduced for one hour. Subsequently, the reaction mixture was firstly poured into ice-cold, saturated, aqueous ammonium chloride solution, acidified cautiously to pH 3 with cold 2N hydrochloric acid and extracted with ethyl acetate. After washing once with water, drying over sodium sulfate and evaporation there was obtained a white, crystalline mass which was recrystallized from ethyl acetate and gave 7 g of 3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid, m.p. 250°-252° C.

Workup

additionSubsequently, the reaction mixture was firstly poured into ice-cold
extractionextracted with ethyl acetate
washAfter washing once with water
dry with materialdrying over sodium sulfate
customevaporation there
customwas obtained a white, crystalline mass which
customwas recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-0833dde5dcd44e279ff441b2ca2671fd
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726191

Linked notes

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