Sodium Methoxide → HCID 87530940, compound

HRID 1260338Notes

Reaction equation

HRID 1260338 reaction equation
[F:1][C:2]1([F:23])[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:22])[O:19][CH2:20][CH3:21])=[CH:10][C:4]=2[O:3]1.C[O-].[Na+]>CO>[F:23][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:22])[O:19][CH2:20][CH3:21])=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 24852735HCID 24852735, compound

Product 1

HCID 87530940HCID 87530940, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 2 (0.35 g, 1.023 mmol) and sodium methoxide (25% wt/wt, 5.11 mmol) in methanol (10 mL) was heated to 50° C. for 2 hours. The mixture was concentrated to dryness under reduced pressure, taken up in DCM (100 mL), washed with water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The residue was purified by column chromatography using DCM as eluant to provide the titled compound. 1H NMR (CDCl3) δ ppm 1.31 (3H), 2.2 (3H), 4.27 (2H), 6.65 (1H), 7.05-7.25 (3H); MS (ESI) 343 (M+H).

Workup

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

Sources & evidence

ORD record
ord-b0eedd7567364b51bcff95dd2cc4938a
Source dataset
uspto-grants-2013_06
Patent number
US08470813B2

Reaction notes

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