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Benzaldehyde → HCID 21099482, Verbindung

HRID 1351668
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1351668
[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
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Komponenten

7

Edukt 3

HCID 240BenzaldehydeHCID 82029Methyl morpholine oxideHCID 21099483[3-({4-[2-(2,4-Difluorophenyl)ethyl]phenyl]sulfonyl)phenyl]methanol

Produkt 1

HCID 21099482HCID 21099482, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178419074HCID 178419074, VerbindungKatalysator
HCID 6344DichloromethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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+].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b671aaa6cd0e4da6afd9511b87433aa9
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07217740B2

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