Cornforth reagent → HCID 58438907, compound

HRID 217453Notes

Reaction equation

HRID 217453 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([CH2:20][OH:21])[CH2:17][CH2:16][C:14]=3[CH:15]=2)[CH:6]=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[F:28][C:2]([F:1])([F:29])[C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[S:12][C:13]3[CH:19]=[C:18]([CH:20]=[O:21])[CH2:17][CH2:16][C:14]=3[CH:15]=2)[CH:6]=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 67364239HCID 67364239, compound

Product 1

HCID 58438907HCID 58438907, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-({[2-(trifluoromethyl)biphenyl-4-yl]oxy}methyl)-4,5-dihydro-1-benzothien-6-yl]methanol (1.0 g) in DCM (20 mL) were added PDC (1.36 g) and MS4 Angstrom (1.36 g) at 25° C. The reaction liquid was stirred for 3 hours, and then filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20) to obtain 2-({[2-(trifluoromethyl)biphenyl-4-yl]oxy}methyl)-4,5-dihydro-1-benzothiophene-6-carbaldehyde (345 mg) as a colorless liquid.

Workup

  1. customThe reaction liquid
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20)

Sources & evidence

ORD record
ord-4477596346f44298a53790438580d0fa
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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