Methanol → HCID 18347211, compound

HRID 2269580Notes

Reaction equation

HRID 2269580 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:11]3[C:12](=[O:15])[O:13][CH2:14][C:10]=3[C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.C[OH:26]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:11]3[C:12](=[O:15])[O:13][CH2:14][C:10]=3[C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:24])=[O:26])=[CH:19][CH:18]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18347203HCID 18347203, compound

Product 1

HCID 18347211HCID 18347211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Fluorophenyl)-3-(4-(methylthio)phenyl)-4H-thieno-[2,3-c]furan-6-one (548 mg) (from Step 4) was dissolved in 10 mL of 10:1 CH2Cl2/-MeOH and treated with 476 mg of MPPM at 0° C. After stirring for 15 min at 0° C. and 1.5 h at room temperature, the reaction mixture was quenched with 20 mL of sat. NaHCO3, and extracted with 50 ml of EtOAc. The extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with EtOAc to give 490 mg of the title compound.

Workup

  1. additiontreated with 476 mg of MPPM at 0° C
  2. customthe reaction mixture was quenched with 20 mL of sat. NaHCO3
  3. extractionextracted with 50 ml of EtOAc
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with EtOAc

Sources & evidence

ORD record
ord-a00d5255d8e449ccb44fe23cb00ff2d9
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

Loading…