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Triethylamine → HCID 21099519, Verbindung

HRID 1351655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1351655
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:18]=1)[CH:16]=O.Cl.[CH3:29][NH:30][CH3:31].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C(O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:15]([CH:18]=1)[CH2:16][N:30]([CH3:31])[CH3:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 21099516HCID 21099516, Verbindung

Produkt 1

HCID 21099519HCID 21099519, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026
Titanium isopropoxide
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5-[(E)-2-(2,4-difluorophenyl)vinyl]-2-(phenylsulfonyl)benzaldehyde (prepared from Example 58 according to the method of Example 50 Step 1, 100 mg, 0.26 mmol), dimethylamine hydrochloride (50 mg, 0.62 mmol), titanium(IV) isopropoxide (0.2 mL, 0.62 mmol) and triethylamine (0.1 mL, 0.62 mmol) in ethanol (2 mL) was stirred at room temperature overnight. Sodium cyanoborohydride (35 mg, 0.56 mmol) was added and the reaction stirred for a further 3 hours. The solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 0–3% methanol/dichloromethane, to give the title compound as a white solid. δH (360 MHz, d6 DMSO): 8.12 (1H, d, J=8.2 Hz), 7.93–7.81 (5H, m), 7.68–7.56 (3H, m), 7.38 (2H, s), 7.33–7.27 (1H, m), 7.14 (1H, td, J=2.4, 8.5 Hz), 3.57 (2H, s), 1.88 (6H, s). m/z (ES+) 414 [MH+].

Aufarbeitung

  1. stirringthe reaction stirred for a further 3 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 0–3% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-57a1a332dde847099a74aaa7e1acbcd5
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07217740B2

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