(Phenylthio)acetic acid, cyclohexyl ester → 1-Ethyl 6-cyclohexyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

HRID 1074042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074042
[CH3:1][N:2]([CH3:23])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[S:5].F[B-](F)(F)F.CN(C)[C:31]([C:37](OCC)=O)=[CH:32][CH:33]=[N+](C)C.C([Li])CCC.C1(SCC(OC2CCCCC2)=O)C=CC=CC=1>CCCCCC.O1CCCC1>[CH3:23][N:2]([CH3:1])[C:3](=[CH:9][CH:10]=[C:11]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:12]([O:14][CH:15]1[CH2:33][CH2:32][CH2:31][CH2:37][CH2:16]1)=[O:13])[C:4]([O:6][CH2:7][CH3:8])=[S:5]

Komponenten

7

Edukt 4

HCID 533051(Phenylthio)acetic acid, cyclohexyl esterHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioateHCID 178418339Butyllithium

Produkt 1

HCID 867435861-Ethyl 6-cyclohexyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

The procedure is as in Example 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (13.7 g), a 1.6M solution (33.1 cc) of n-butyllithium in hexane and cyclohexyl (phenylthio)acetate (12 g) in tetrahydrofuran (150 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent, 1-ethyl 6-cyclohexyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate (9.7 g) is obtained, and is used in the crude state in the subsequent phases.

Aufarbeitung

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-0ba37e7ddf124822bf0c423b41ac72ab
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971979

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