Ethanol → 3-[4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-phenyl]-acrylic acid

HRID 1992964Notes

Reaction equation

C([O:3][C:4](=[O:32])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]([CH3:26])[C:15]=2[C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:9][CH:8]=1)C.[OH-].[Na+].CCO>C1COCC1>[CH3:25][O:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[C:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:4]([OH:32])=[O:3])=[CH:12][CH:11]=1)=[C:15]([C:27]1[CH:31]=[CH:30][S:29][CH:28]=1)[C:16]([CH3:26])=[CH:17]2

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 3-[4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-phenyl]-acrylic acid ethyl ester (201) (0.27 g, 0.61 mmol), 1 N NaOH (5 mL), EtOH (4 mL), THF (4 mL) was heated at 60° C. for 2.5 h. Reaction mixture was cooled to room temperature and quenched with 20% HCl then extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified with 1.5% to 3.5% MeOH in DCM over 30 min to give 0.25 g (99%) of the title compound (202) as a white foam. 1H NMR (400 MHz, d-CDCl3): δ 2.31 (s, 3H), 3.92 (s, 3H), 6.24 (d, J=16 Hz, 1H), 6.64 (d, J=8.8 Hz, 2H), 6.90-6.92 (m, 1H), 7.02-7.05 (m, 2H), 7.12 (m, 1H), 7.21-7.23 (m, 1H), 7.31 (d, J=8.6 Hz, 2H), 7.56 (m, 1H), 7.64 (d, J=15.9 Hz, 1H), 7.71 (d, J=9.2 Hz, 1H).

Workup

customReaction mixture
temperaturewas cooled to room temperature
customquenched with 20% HCl
extractionthen extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified with 1.5% to 3.5% MeOH in DCM over 30 min

Sources & evidence

ORD record: ord-82d0792d8f444c96ac89933356433373
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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