Sodium Hydroxide → HCID 68539395, compound

HRID 1992926Notes

Reaction equation

HRID 1992926 reaction equation
[CH:1]1([C:4]2[C:5]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:6]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=3)[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CCO>[CH:1]1([C:4]2[C:5]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:6]([O:16][C:17]3[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=3)[C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=3)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616662HCID 86616662, compound

Product 1

HCID 68539395HCID 68539395, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (154) (0.21 g, 0.45 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.19 g (96%) of the title compound (155) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.75-0.85 (m, 4H), 1.60-1.70 (m, 1H), 3.92 (s, 3H), 6.22 (d, J=15.9 Hz, 1H), 6.60 (d, J=8.6 Hz, 2H), 7.02 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.13 (d, J=2.2 Hz, 1H), 7.18-7.30 (m, 8H), 7.62 (d, J=15.9 Hz, 1H), 7.68 (d, J=8.9 Hz, 1H). LCMS (APCI): m/z 437 (M+H)+, m/z 435 (M−H)−.

Sources & evidence

ORD record
ord-dbd87f6e41224f59af0f0a41116d37ce
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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