Sodium Hydroxide → HCID 11517134, compound

HRID 1992920Notes

Reaction equation

HRID 1992920 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:6]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2.[OH-].[Na+]>C1COCC1.CCO>[CH3:1][O:2][CH2:3][C:4]1[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:6]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616660Ethyl (2E)-3-[4-({3-[(methyloxy)methyl]-2-phenyl-1-naphthalenyl}oxy)phenyl]-2-propenoate

Product 1

HCID 11517134HCID 11517134, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (147) (20 mg, 0.046 mmol) was saponified with 1 N NaOH in THF and EtOH to give 18 mg (93%) of the title compound (148) as an off-white solid. mp 76-79° C. 1H NMR (400 MHz, CDCl3): δ 3.33 (s, 3H), 4.31 (s, 2H), 6.22 (d, J=15.9 Hz, 1H), 6.60 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 2H), 7.20-7.30 (m, 5H), 7.44 (t, J=7.9 Hz, 1H), 7.52 (t, J=7.5 Hz, 1H), 7.62 (d, J=15.9 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.93 (d, J=8.2 Hz, 1H), 7.95 (s, 1H). LCMS (ESI): m/z 433 (M+Na)+, m/z 409 (M−H)−. HRMS (EI) Calc for C27H22O4: 411.1596 (M+•). Found: 411.1606.

Sources & evidence

ORD record
ord-454d83341a6e4f42803af5d0b5e66ebc
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…