Hydrochloric Acid → 2-Biphenyl-3-yl-4-methylpent-4-enoic acid

HRID 1060736

Reaction equation

[Li+].CC([N-]C(C)C)C.[C:9]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=1.Br[CH2:26][C:27]([CH3:29])=[CH2:28].Cl>C1COCC1.C(OCC)(=O)C>[C:9]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]([CH2:28][C:27]([CH3:29])=[CH2:26])[C:16]([OH:18])=[O:17])[CH:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of LDA (2.2 mL, 2.0 M in THF) in THF (20 mL) was cooled to 0° C. and then treated with biphenyl-3-ylacetic acid (0.212 g, 1.0 mmol). The mixture was stirred for 40 minutes, cooled to −78° C. and then treated with 3-bromo-2-methylpropene (135 μL, 1.3 mmol). The mixture was stirred for 1 hour, treated with 1 M hydrochloric acid (5 mL) and then diluted with ethyl acetate (50 mL). The organic layer was separated washed with water, brine, dried (MgSO4) and concentrated. Product was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane to provide 2-biphenyl-3-yl-4-methylpent-4-enoic acid (250 mg, 0.93 mmol). 1H NMR (DMSO-d6): 1.71 (s, 3H), 2.52 (m, 2H), 3.68 (dd, 1H), 4.75 (m, 2H), 7.08 (d, 1H), 7.28-7.37 (m, 8H). LCMS: 267.1 (M+H+).

Workup

stirringThe mixture was stirred for 1 hour
customThe organic layer was separated
washwashed with water, brine
dry with materialdried (MgSO4)
concentrationconcentrated
customProduct was purified from the residue by flash column on silica gel (60° A) with 33% ethyl acetate in hexane

Sources & evidence

ORD record: ord-89201b9873bf45019bed15b90d7f7985
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525036B2

Linked notes

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