Sodium Hydroxide → HCID 68536111, compound

HRID 1992875Notes

Reaction equation

HRID 1992875 reaction equation
[CH2:1]([C:5]1[C:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CCO>[CH2:1]([C:5]1[C:6]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616650HCID 86616650, compound

Product 1

HCID 68536111HCID 68536111, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester 83 (0.30 g, 0.62 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.24 g (86%) of the title compound (84) as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.77 (t, J=7.3 Hz, 3H), 1.10-1.28 (m, 2H), 1.40-1.50 (m, 2H), 2.50-2.60 (m, 2H), 3.93 (s, 3H), 6.22 (d, J=16.0 Hz, 1H), 6.58 (d, J=8.6 Hz, 2H), 7.04 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.08-7.15 (m, 2H), 7.16 (d, J=2.4 Hz, 1H), 7.18-7.30 (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 453 (M+H)+, m/z 451 (M−H)−.

Sources & evidence

ORD record
ord-eadc032a3731462e8be989b073a4e2f1
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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