Methanol → HCID 15390785, compound

HRID 1019177Notes

Reaction equation

HRID 1019177 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:20])[CH2:11][C:12]2[CH:17]=[CH:16][C:15](SC)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.O[O:23][S:24]([O-:26])=O.[K+].[CH3:28]O>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:20])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:24]([CH3:28])(=[O:26])=[O:23])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 15390784HCID 15390784, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15390785HCID 15390785, compound

Procedure

To 7.10 g of 4-(2-(4-methylthiophenyl)-1-oxo-ethyl)benzoic acid methyl ester in MeOH (100 mL) was added oxone (21.0 g) in H20 (20.0 mL) at 0° C. After a few hours at r.t., the reaction mixture was extracted with EtOAc and H2O to afford after flash chromatography (50 to 100% EtOAc in hexane), the title product as a white solid (3.20 g). 1H NMR (CD3COCD3) d 3.10 (3H, s), 3.95 (3H, s), 4.65 (2H, s), 7.60 (2H, d), 7.96 (2H, d), 8.20 (4H, q).

Workup

  1. waitAfter a few hours at r.t.
  2. extractionthe reaction mixture was extracted with EtOAc and H2O
  3. customto afford after flash chromatography (50 to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-f37b0c913ee14f71a3d966f4dfcc6b3f
Source dataset
uspto-grants-2002_11
Patent number
US06486194B2

Reaction notes

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