Triethylamine → 1,1-Dimethylethyl(2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenyl}-2-propenoate

HRID 2100050

Reaktionsgleichung

Reaktionsgleichung von HRID 2100050
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([C:8](=[C:16]2[CH2:21][CH2:20][S:19][CH2:18][CH2:17]2)[C:5]2[CH:6]=[CH:7][C:2](/[CH:24]=[CH:23]/[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 686544294-[(4-Bromophenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenol

Produkt 1

HCID 689782991,1-Dimethylethyl(2E)-3-{4-[(4-hydroxyphenyl)(tetrahydro-4H-thiopyran-4-ylidene)methyl]phenyl}-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Reagents 36 (0.32 g, 0.886 mmol), t-butyl acrylate (0.78 mL, 5.31 mmol), Pd(OAc)2 (0.042 g, 0.186 mmol), P(o-tolyl)3 (0.12 g, 0.381 mmol) and Et3N (0.74 mL, 5.31 mmol) were added to a flask containing CH3CN (13 mL) and the reaction mixture was heated at 85° C. for 24 h. The reaction mixture was allowed to cool at RT and partitioned between water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the filtrate was concentrated to give the crude product. The crude product was purified by flash column chromatography on silica gel using a hexanes:EtOAc gradient (100:0 to 50:50) to give compound 37 as a yellow foam. 1H NMR (400 MHz, DMSO-d6): δ 1.46 (s, 9H), 2.65-2.66 (m, 5H), 6.45 (d, J=16 Hz, 1H), 6.68 (d, J=8.4 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.1 Hz, 2H), 7.49 (d, J=16.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 2H), 9.37 (s, 1H).

Aufarbeitung

  1. temperatureto cool at RT
  2. custompartitioned between water and EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customto give the crude product
  9. customThe crude product was purified by flash column chromatography on silica gel using a hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a7783ce1f834456bb17e8f98adf70b67
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569601B2

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