HCID 69217569, compound → HCID 72469341, compound

HRID 1394576Notes

Reaction equation

COC[O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([CH2:15][CH3:16])=[CH:7][C:6]=1[C:17]1[CH:31]=[CH:30][C:20]2[O:21][C:22]([C:24]([CH3:29])=[CH:25][C:26]([OH:28])=[O:27])=[CH:23][C:19]=2[CH:18]=1>C1COCC1.CO>[OH:4][C:5]1[C:10]([C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][C:8]([CH2:15][CH3:16])=[CH:7][C:6]=1[C:17]1[CH:31]=[CH:30][C:20]2[O:21][C:22]([C:24]([CH3:29])=[CH:25][C:26]([OH:28])=[O:27])=[CH:23][C:19]=2[CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 9 mg (0.021 mmol) of 3-[5-(2-methoxymethoxy-3-tert-butyl-5-ethylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid in 0.5 mL of THF, 0.5 mL of methanol and 2 mL of 6 N aqueous HCL was heated to 40° C. overnight. The solvents were evaporated and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude acid is directly recrystallized from acetonitrile to afford 5 mg (0.013 mmol, yield: 62%) of 3-[5-(2-hydroxy-3-tert-butyl-5-ethylphenyl)-benzo[b]furan-2-yl]-but-2-enoic acid as a white solid. 1H NMR (CDCl3), δ: 7.67 (s, 1H), 7.59 (dd, J=8.4, 2.0 Hz, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.14 (s, 1H), 7.09 (s, 1H), 6.94 (s, 1H), 6.73 (s, 1H), 3.80 (broad s, 1H), 2.64 (dd, J=15.2, 7.4 Hz, 2H), 2.59 (s, 3H), 1.45 (s, 9H), 1.25 (t, J=7.5 Hz, 3H).

Workup

customThe solvents were evaporated
extractionthe aqueous layer was extracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customthe solvents were removed under reduced pressure
customThe crude acid is directly recrystallized from acetonitrile

Sources & evidence

ORD record: ord-4eb1e301de32416aa83fe745ed0e9884
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

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