Sodium Hydroxide → HCID 9843478, compound

HRID 1270211Notes

Reaction equation

HRID 1270211 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:28])[C:11]#[C:12][C:13]2[CH:18]=[C:17]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[C:16]([O:24][CH3:25])=[CH:15][C:14]=2[O:26][CH3:27])=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:27][O:26][C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:18][C:13]=1[C:12]#[C:11][C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[O:2])=[CH:9][CH:8]=1)=[O:28]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10287620HCID 10287620, compound

Product 1

HCID 9843478HCID 9843478, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-benzoic acid methyl ester (50 mg, 0.12 mmol) from Ex-1 was dissolved in THF (2 mL) and methanol (2 mL). Sodium hydroxide solution (1 N, 1 mL) was added and the resulting solution was stirred at room termperature under nitrogen for 1 h. The reaction was then diluted with water (10 mL) and washed with ethyl acetate (10 mL). The aqueous phase was acidified with conc. HCl and extracted with ethyl acetate (2×10 mL). The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to afford 20 mg (42%) of the desired 4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-benzoic acid as a yellow solid, m.p. 220° C. with decomposition. 1H-NMR (300 MHz, d6-DMSO) δ 8.30 (d, 2H, J=8.0 Hz), 8.14 (d, 2H, J=8.0 Hz), 8.01 (s, 1H), 7.58 (m, 1H), 7.50 (m, 1H), 7.08 (m, 1H), 6.88 (s, 1H), 4.04 (s, 3H), 4.02 (s, 3H); EIMS m/z 392 (M+).

Workup

  1. washwashed with ethyl acetate (10 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b77af101349a4d6c8993d822f44defb7
Source dataset
uspto-grants-2007_04
Patent number
US07202247B2

Reaction notes

Loading…