Sodium methanethiolate → HCID 21107105, compound

HRID 1765398Notes

Reaction equation

HRID 1765398 reaction equation
[CH3:1][S-:2].[Na+].F[C:5]1[C:10]2[C:11](=[O:23])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:13][O:14][C:9]=2[CH:8]=[C:7]([O:24][CH3:25])[CH:6]=1>C1COCC1>[CH3:25][O:24][C:7]1[CH:6]=[C:5]([S:2][CH3:1])[C:10]2[C:11](=[O:23])[C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:13][O:14][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 21107100HCID 21107100, compound

Product 1

HCID 21107105HCID 21107105, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium thiomethoxide (600 mg) was added to a solution of 5-fluoro-7-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran (325 mg) in THF (10 mL). The mixture was refluxed for 1 h and cooled. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over MgSO4. Purification by chromatography on silica gel (eluant: ethyl acetate-chloroform, gradient from 0:100 to 5:95) gave the title compound (310 mg) as a pale yellow solid. 1H NMR (CDCl3): 7.81 (s, 1H), 7.50 (d, 2H, J=8.7 Hz), 6.95 (d, 2H, J=8.7 Hz), 6.67 (d, 1H, J=2.1 Hz), 6.59 (d, 1H, J=2.1 Hz), 3.91 (s, 3H), 3.83 (s, 3H); MS: 329 (MH+); HPLC tR: 2.68 min.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customPurification by chromatography on silica gel (eluant: ethyl acetate-chloroform, gradient from 0:100 to 5:95)

Sources & evidence

ORD record
ord-72a89650e6f64803a6c5f0c700c6dea1
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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