Sodium Hydroxide → HCID 68536417, compound

HRID 1992914Notes

Reaction equation

HRID 1992914 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:32][CH2:33][CH3:34])[C:8]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:9]2[O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:35][CH3:36].[OH-].[Na+]>C1COCC1.CCO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:32][CH2:33][CH3:34])[C:8]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:9]2[O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[O:35][CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616659HCID 86616659, compound

Product 1

HCID 68536417HCID 68536417, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (139) (0.44 g, 0.91 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.33 g (80%) of the title compound (140) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.80 (t, J=7.3 Hz, 3H), 1.40-1.55 (m, 2H), 2.52 (t, J=7.8 Hz, 2H), 4.01 (s, 3H), 6.23 (d, J=15.9 Hz, 1H), 6.55 (d, J=8.8 Hz, 2H), 7.06-7.12 (m, 2H), 7.20-7.30 (m, 6H), 7.41 (d, J=12.1 Hz, 1H), 7.56 (s, 1H), 7.62 (d, J=15.9 Hz, 1H). LCMS (APCI): m/z 457 (M+H)+, m/z 455 (M−H)−.

Sources & evidence

ORD record
ord-f100bb393f75469e9fdf47b48940ffd6
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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