Sodium Hydroxide → HCID 68537193, compound

HRID 1992845Notes

Reaction equation

HRID 1992845 reaction equation
[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.[OH-].[Na+]>C1COCC1.CCO>[CH3:1][C:2]1[C:3]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[C:4]([O:14][C:15]2[CH:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616645HCID 86616645, compound

Product 1

HCID 68537193HCID 68537193, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using the procedure described in Example 1 (Step 10), ethyl ester (47) (0.33 g, 0.69 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.26 g (85%) of compound (48) as an off-white foam. 1H NMR (400 MHz, CDCl3): δ 2.25 (s, 3H), 3.77 (s, 3H), 3.92 (s, 3H), 6.22 (d, J=16.0 Hz, 1H), 6.61 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.6 Hz, 2H), 7.00-7.07 (m, 3H), 7.12 (d, J=2.5 Hz, 1H), 7.28 (d, J=8.7 Hz, 2H), 7.56 (s, 1H), 7.63 (d, J=15.9 Hz, 1H), 7.68 (d, J=9.2 Hz, 1H). LCMS (APCI): m/z 441 (M+H)+.

Sources & evidence

ORD record
ord-b6bc564fcd7a4dd9b8e37afadf40b226
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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