Sodium Hydroxide → HCID 68536302, compound

HRID 1992908Notes

Reaction equation

HRID 1992908 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:16][CH2:17][CH3:18])[CH2:10][C:11]([O:13]CC)=[O:12])=[CH:4][C:3]=1[O:19][CH3:20].[OH-].[Na+]>C1COCC1.CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:16][CH2:17][CH3:18])[CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68539528HCID 68539528, compound

Product 1

HCID 68536302HCID 68536302, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (131) (2.14 g, 7.58 mmol) was saponified with 1 N NaOH in THF and EtOH to give 1.92 g (˜100%) of the title compound (132) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.88 (t, J=7.0 Hz, 3H), 1.25-1.45 (m, 4H), 2.05-2.20 (m, 1H), 2.20-2.35 (m, 2H), 2.45-2.55 (m, 1H), 2.60-2.70 (m, 1H), 3.87 (s, 3H), 6.64-6.70 (m, 1H), 6.76 (dd, J1=8.2 Hz, J2=1.8 Hz, 1H), 6.96 (dd, J1=11.3 Hz, J2=8.2 Hz, 1H). LCMS (ESI): m/z 253 (M−H)−.

Sources & evidence

ORD record
ord-ee26164e03c94e77b0d830d372e63afa
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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