Sodium Hydroxide → HCID 68536194, compound

HRID 1992906Notes

Reaction equation

HRID 1992906 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]([O:24]CC)=[O:23])=[CH:16][CH:15]=1)=[C:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]([CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[CH:6]2.[OH-].[Na+]>C1COCC1.CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[CH:18][CH:19]=1)=[C:8]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:7]([CH2:33][CH2:34][C:35]([F:36])([F:38])[F:37])=[CH:6]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616657HCID 86616657, compound

Product 1

HCID 68536194HCID 68536194, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (127) (0.34 g, 0.65 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.28 g (88%) of the title compound (128) as a white solid. 1H NMR (400 MHz, CDCl3): δ 2.10-2.25 (m, 2H), 2.80-2.90 (m, 2H), 3.94 (s, 3H), 6.22 (d, J=15.9 Hz, 1H), 6.57 (d, J=8.6 Hz, 2H), 7.06-7.14 (m, 3H), 7.17 (d, J=2.4 Hz, 1H), 7.22-7.30 (m, 5H), 7.59 (s, 1H), 7.62 (d, J=15.9 Hz, 1H), 7.72 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 493 (M+H)+, m/z 491 (M−H)−.

Sources & evidence

ORD record
ord-75e98f1e2e4643259ac6dd42a5551b39
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…