Potassium Carbonate → (E)-3-(3'-Adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester

HRID 41726

Reaktionsgleichung

Reaktionsgleichung von HRID 41726
[C:1]([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:39]([O:42][C:43](=[O:47])[O:44][CH2:45]I)[CH2:40][CH3:41]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:1]([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:45][O:44][C:43]([O:42][CH2:39][CH2:40][CH3:41])=[O:47])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 11042958Iodomethyl 2-(methyl)ethyl carbonateHCID 86660473HCID 86660473, Verbindung

Produkt 1

HCID 67426176(E)-3-(3'-Adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (E)-3-(3′-adamantan-1yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester (250 mg, 0.581 mmol) and K2CO3 (241 mg, 1.74 mmol) in water (2.9 ml) was stirred at RT for 30 min. Tetrabutylammonium hydrogen sulfate (197 mg, 0.581 mmol) and DCM (1.4 ml) were then added and the stirring maintained for further 10 min. A solution of carbonic acid iodomethyl ester propyl ester (184 mg, 0.755 mmol) in DCM (1.4 ml) was then added dropwise. The biphasic solution was stirred overnight at RT. After standard work-up and removal of the solvent under reduced pressure, the residue was taken up in Et2O. Tetrabutylammonium iodide was filtered off and the solvent was evaporated. (E)-3-(3′-Adamantan-1-yl-4′-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester was obtained (117 mg, 36%) after purification on silica gel (EtOAc/hexane 12:88).

Aufarbeitung

  1. temperaturethe stirring maintained for further 10 min
  2. stirringThe biphasic solution was stirred overnight at RT
  3. customAfter standard work-up and removal of the solvent under reduced pressure
  4. filtrationTetrabutylammonium iodide was filtered off
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b52aefb45520443ca761841de668ff7c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530517B2

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