Methanol → 3-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid

HRID 659113Notes

Reaction equation

HRID 659113 reaction equation
C[O:2][C:3](=[O:27])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:17][C:15]=3[N:16]=2)[CH:7]=1.CO.[OH-].[Na+]>C1COCC1>[C:21]1([C:18]2[CH:19]=[CH:20][C:14]3[O:13][C:12]([C:8]4[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:27])=[O:2])[CH:11]=[CH:10][CH:9]=4)=[N:16][C:15]=3[CH:17]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 684169753-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid methyl ester

Product 1

HCID 684142043-[3-(5-Phenyl-benzoxazol-2-yl)-phenyl]-acrylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester (33) (41 mg, 0.12 mmol) was hydrolysed using Method C, except that MeOH (3 mL), THF (3 mL) and 1M NaOH (5 mL) were used, and the reaction was stirred for 2 hours. Yield: 21 mg, 53%; LC-MS tr 1.74 min; HPLC Purity: 96%; MS (ES+) m/z 342 (M+H); 1H NMR (400 MHz; DMSO): δ 6.7 (d, 1H), 7.4 (t, 1H), 7.45-7.55 (t, 2H), 7.70-7.80 (m, 5H), 7.9 (d, 1H), 8.05 (d, 1H), 8.10 (s, 1H), 8.30 (d, 1H), 8.50 (s, 1H), 12.55 (br. s, 1H)

Workup

  1. waitLC-MS tr 1.74 min

Sources & evidence

ORD record
ord-1cbcba417ca24b8fb7e52db701996fee
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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