Sodium Hydroxide → HCID 11516447, compound

HRID 1992878Notes

Reaction equation

HRID 1992878 reaction equation
[CH3:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:4]([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)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[Na+]>C1COCC1.CCO>[CH3:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:4]([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)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616651HCID 86616651, compound

Product 1

HCID 11516447HCID 11516447, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester 88 (123 mg, 0.30 mmol) was saponified with 1 N NaOH in THF and EtOH to give 90 mg (79%) of the title compound (89) as a white solid. mp 224-225° C. 1H NMR (400 MHz, CDCl3): δ 2.26 (s, 3H), 6.22 (d, J=16.0 Hz, 1H), 6.61 (d, J=8.8 Hz, 2H), 7.10-7.16 (m, 2H), 7.20-7.30 (m, 5H), 7.38 (t, J=7.4 Hz, 1H), 7.49 (t, J=7.2 Hz, 1H), 7.62 (d, J=15.9 Hz, 1H), 7.68 (s, 1H), 7.80 (d, J=8.5 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H). LCMS (ESI): m/z 381 (M+H)+, m/z 379 (M−H)−. Anal. Calc for C26H20O3.0.33H2O: C, 80.81; H, 5.39. Found: C, 80.73; H, 5.03.

Sources & evidence

ORD record
ord-042e4f119eb8416291fbbcbe744c596e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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