Benzaldehyde → HCID 21099482, compound

HRID 2376983Notes

Reaction equation

HRID 2376983 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:21]=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(=O)C1C=CC=CC=1.C[N+]1([O-])CCOCC1>ClCCl.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=2)[CH:26]=[O:27])(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 82029Methyl morpholine oxideHCID 210994833-[[4-[2-(2,4-Difluorophenyl)ethyl]phenyl]sulfonyl]benzenemethanol

Product 1

HCID 21099482HCID 21099482, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-({4-[2-(2,4-difluorophenyl)ethyl]phenyl]sulfonyl)phenyl]methanol (prepared from 3-({4-[E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzaldehyde (Example 50 Step 1) according to the method of Example 117) in dichloromethane (4 mL) was added 4 Å molecular sieves (0.1 g) and the mixture stirred for 10 minutes. 4-Methylmorpholine N-oxide (68 mg, 0.58 mmol) was added in one portion and the reaction stirred for 10 minutes, then tetrapropylammonium perruthenate (6.9 mg, 0.02 mmol) added. The reaction was stirred for 30 minutes then diluted with ethyl acetate, filtered through a pad of silica and washed with further ethyl acetate. The filtrate was evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to yield 3-({4-[2-(2,4-difluorophenyl)ethyl]phenyl)sulfonyl)benzaldehyde (103 mg, 68%). δH (400 MHz, CDCl3): 10.06 (1H, s), 8.40 (1H, s), 8.18 (1H, d, J=7.8 Hz), 8.07 (1H, d, J=7.6 Hz), 7.87 (2H, d, J=8.3 Hz), 7.69 (1H, t, J=7.7 Hz), 7.30 (2H, d, J=8.2 Hz), 6.99 (1H, q, J=7.9 Hz), 6.79-6.73 (2H, m), 2.95-2.87 (4H, m). m/z (ES+) 387 [MH+].

Workup

  1. additionwas added 4 Å molecular sieves (0.1 g)
  2. stirringthe reaction stirred for 10 minutes
  3. stirringThe reaction was stirred for 30 minutes
  4. filtrationfiltered through a pad of silica
  5. washwashed with further ethyl acetate
  6. customThe filtrate was evaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 25% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-67bc646a7b544a44a866267321f4432c
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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