Water → HCID 178451367, Verbindung

HRID 1035723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035723
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.CCN(C(C)C)C(C)C.[OH2:39].[O:40]1[CH2:45]COCC1>CN(C1C=CN=CC=1)C.ClCCl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:24]([O:23][C:21]([CH2:20][O:19][C@H:16]1[CH2:17][CH2:18][C@H:13]([C:10]2[CH:11]=[CH:12][C:7]([C:45]([OH:40])=[O:39])=[CH:8][CH:9]=2)[CH2:14][CH2:15]1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Komponenten

10

Edukt 4

HCID 962WaterHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 178451369HCID 178451369, Verbindung

Produkt 1

HCID 178451367HCID 178451367, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 178521658HCID 178521658, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

250 mg of tert-butyl trans-[4-(4-trifluoromethanesulfonyloxyphenyl)cyclohexyloxy]-acetate are placed in 1.5 mL of dioxane in a microwave tube. 83 mg of hexacarbonylmolybdenum (0.32 mmol, 0.5 eq.), 14 mg of palladium diacetate (0.06 mmol, 0.1 eq.), 35 mg of DPPF (0.06 mmol, 0.1 eq.), 154 mg of DMAP (1.26 mmol, 2 eq.), 0.25 mL of DIEA (1.45 mmol, 2.3 eq.) and 0.23 mL of water are successively added. The tube is sealed and heated by microwave at 120° C. for 30 minutes. The reaction medium is diluted with dichloromethane and washed three times with saturated aqueous sodium carbonate solution. The reaction medium is diluted with diethyl ether and washed with aqueous 5N HCl solution. The organic phases are combined and evaporated to give 270 mg of trans-4-(4-tert-butoxycarbonylmethoxycyclohexyl)benzoic acid, which is used without further purification in the following step.

Aufarbeitung

  1. customThe tube is sealed
  2. washwashed three times with saturated aqueous sodium carbonate solution
  3. additionThe reaction medium is diluted with diethyl ether
  4. washwashed with aqueous 5N HCl solution
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4a7f36292d2349c3852481c62ba55174
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546391B2

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