Sodium Hydroxide → HCID 68537308, compound

HRID 1992868Notes

Reaction equation

HRID 1992868 reaction equation
[CH3:1][CH:2]([C:4]1[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:3].[OH-].[Na+]>C1COCC1.CCO>[CH3:3][CH:2]([C:4]1[C:5]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH3:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616649HCID 86616649, compound

Product 1

HCID 68537308HCID 68537308, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester 74 (0.45 g, 0.97 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.33 g (78%) of the title compound (75) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.19 (d, J=6.8 Hz, 6H), 2.90 (sept, J=6.8 Hz, 1H), 3.94 (s, 3H), 6.22 (d, J=15.9 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 7.04 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.06-7.15 (m, 2H), 7.18-7.30 (m, 6H), 7.62 (d, J=16.0 Hz, 1H), 7.65 (s, 1H), 7.69 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+.

Sources & evidence

ORD record
ord-5b0f6c0e178b44fa9825b0ceb729feea
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…