Benzenepropanoic acid → HCID 12740364, compound

HRID 1927283Notes

Reaction equation

[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C([Li])CCC.[C:12]1([CH2:18][CH2:19]C(Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(CCC(O)=O)C=CC=CC=1>O1CCCC1.S(Cl)(Cl)=O>[O:6]=[C:4]([CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of cyanoacetic acid (1.0 g, 11.8 mmol) in tetrahydrofuran (20 mL) was cooled to −78° C. and treated with 1.6 M n-butyl lithium in hexanes (14.7 mL, 23.5 mmol). The mixture was warmed to −20° C. over 2 hours, cooled to −78° C. and treated with 3-phenylpropionyl chloride (prepared by refluxing a solution of 3-phenylpropionic acid (1.0 g, 6.7 mmol) in thionyl chloride (4 mL) for 3 hours, evaporating and drying). The mixture was stirred at −78° C. for 1 hour and 20% hydrochloric acid added until the pH=3. The mixture was diluted with diethyl ether, washed with saturated sodium bicarbonate, and the organic layer separated and concentrated. The crude product was purified by flash chromatography on silica gel using 0-50% ethyl acetate/hexanes to provide the title compound. MS (ESI) m/e 191 (M+H+NH3).

Workup

temperaturecooled to −78° C.
customprepared
customevaporating
customdrying)
addition20% hydrochloric acid added until the pH=3
additionThe mixture was diluted with diethyl ether
washwashed with saturated sodium bicarbonate
customthe organic layer separated
concentrationconcentrated
customThe crude product was purified by flash chromatography on silica gel using 0-50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-76a61b00b8424ba59897327eaa48cb5f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183250B2

Reaction notes

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