Sodium Methoxide → HCID 11469378, compound

HRID 1019179Notes

Reaction equation

HRID 1019179 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:14])[CH2:10][CH2:11][CH:12]=O)=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:14])[CH2:10][CH2:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18400184HCID 18400184, compound

Product 1

HCID 11469378HCID 11469378, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8 g of 1-(4-fluorophenyl)-5-oxo-2-pentanone in 300 mL of MeOH was treated with 2 g of NaOMe. The mixture was stirred for 2 h and then quenched with 5 mL of HOAc. The solvent was evaporated and the residue purified by flash chromatography, eluting with 3:1 hexane/EtOAc to give 7 g of the title product. 1H NMR (CDCl3) d 2.57 (2H, m), 2.68 (2H, m), 7.04 (2H, J=8.8 Hz, t), 7.67 (2H, J=8.8, 5.5 Hz, dd), 7.77 (1H, m).

Workup

  1. customquenched with 5 mL of HOAc
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography
  4. washeluting with 3:1 hexane/EtOAc

Sources & evidence

ORD record
ord-1408619e11c04311964813dd78b48396
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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