Sodium Hydroxide → HCID 10311032, compound

HRID 1270213Notes

Reaction equation

HRID 1270213 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([C:14](=[O:32])[C:15]#[C:16][C:17]2[CH:22]=[C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)[C:20]([O:28][CH3:29])=[CH:19][C:18]=2[O:30][CH3:31])=[CH:8][C:7]=1[O:33][CH3:34].[OH-].[Na+]>C1COCC1.CO.Cl.C(OC(C)C)(=O)C>[CH3:31][O:30][C:18]1[CH:19]=[C:20]([O:28][CH3:29])[C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[CH:22][C:17]=1[C:16]#[C:15][C:14]([C:9]1[CH:10]=[C:11]([O:12][CH3:13])[C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]([O:33][CH3:34])[CH:8]=1)=[O:32]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 10195869HCID 10195869, compound

Product 1

HCID 10311032HCID 10311032, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 7915Isopropyl AcetateSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ex-4: {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-2,6-dimethoxy-phenoxy}-acetic acid methyl ester (500 mg, 1.01 mmol) from Ex-3 was dissolved in THF (5 mL) and methanol (5 mL). Sodium hydroxide solution (1 N, 5 mL) was added and the resulting solution was stirred at room termperature under nitrogen for 30 min. The reaction-was then diluted with 1 N HCl and isopropyl acetate and the layers cut. The organic phase was concentrated to dryness under reduced pressure, diluted with a small amount of ethanol and filtered to afford 350 mg (73%) of the desired {4-[3-(2,4-dimethoxy-5-thiophen-2-yl-phenyl)-propynoyl]-2,6-dimethoxy-phenoxy}-acetic acid as a yellow solid, m.p. 192–194° C. 1H-NMR (300 MHz, d6-DMSO) δ 7.95 (s, 1H), 7.56 (dd, 1H, J=3.5 and 1.4 Hz), 7.49 (m, 1H), 7.47 (s, 2H), 7.07 (dd, 1H, J=5.1 and 3.5 Hz), 6.86 (s, 1H), 4.61 (s, 2H), 4.00 (s, 3H), 3.97 (s, 3H), 3.84 (s, 6H).

Workup

  1. customThe reaction-was
  2. concentrationThe organic phase was concentrated to dryness under reduced pressure
  3. additiondiluted with a small amount of ethanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9a43dcee2fda4b62b74e8ca3390b4eea
Source dataset
uspto-grants-2007_04
Patent number
US07202247B2

Reaction notes

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