Sodium Methoxide → HCID 178474508, compound

HRID 1260340Notes

Reaction equation

HRID 1260340 reaction equation
[F:1][C:2]1([F:21])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C:14](=[CH2:16])[S:13]/[C:12]/3=[N:17]\[C:18](=[O:20])[CH3:19])=[CH:10][C:4]=2[O:3]1.C[O-].[Na+]>CO>[F:21][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:15]=[C:14]([CH3:16])[S:13]/[C:12]/3=[N:17]\[C:18](=[O:20])[CH3:19])=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178429856HCID 178429856, compound

Product 1

HCID 178474508HCID 178474508, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 5 (2.0 g, 6.4 mmol) and sodium methoxide (25% wt/wt, 32.02 mmol) in methanol (25 mL) was heated to 50° C. for two hours. The mixture was concentrated to dryness under reduced pressure, diluted with DCM (300 mL), and washed with water (200 mL) and brine (200 mL). The organic phase was dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The residue was purified by column chromatography using mixture DCM-MeOH (95:5) as eluant to provide the titled compound. 1H NMR (CDCl3) δ ppm 2.24 (3H), 2.32 (3H), 6.75 (1H), 7.05-7.35 (3H); MS (ESI) 313 (M+H).

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. additiondiluted with DCM (300 mL)
  3. washwashed with water (200 mL) and brine (200 mL)
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ac79cde870724299b5dc69622b607a30
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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