Sodium Hydroxide → HCID 68536346, compound

HRID 1992899Notes

Reaction equation

HRID 1992899 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][CH2:35][CH2:36][CH3:37])=[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:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:6]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616655HCID 86616655, compound

Product 1

HCID 68536346HCID 68536346, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (115) (0.48 g, 0.97 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.42 g (93%) of the title compound (116) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=6.8 Hz, 3H), 1.10-1.25 (m, 4H), 1.40-1.55 (m, 2H), 2.53 (t, J=7.8 Hz, 2H), 3.93 (s, 3H), 6.22 (d, J=16.0 Hz, 1H), 6.58 (d, J=8.8 Hz, 2H), 7.04 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.08-7.14 (m, 2H), 7.16 (d, J=2.4 Hz, 1H), 7.19-7.30 (m, 5H), 7.58 (s, 1H), 7.62 (d, J=15.9 Hz, 1H), 7.69 (d, J=9.2 Hz, 1H). LCMS (ESI): m/z 467 (M+H)+, m/z 465 (M−H)−.

Sources & evidence

ORD record
ord-c2fe6ba450df49159991c22fe64a47ee
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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