Acetic acid, (phenylthio)-, ethyl ester → 6-Ethyl 1-tert-butyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

HRID 477363

Reaktionsgleichung

Reaktionsgleichung von HRID 477363
CN(C)C(=CC=[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(OCC)=S.F[B-](F)(F)F.[CH3:29][N:30]([CH3:44])[C:31]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=O)=[CH:32][CH:33]=[N+](C)C.C([Li])CCC.C1([S:56]CC(OCC)=O)C=CC=CC=1>CCCCCC.O1CCCC1>[CH3:29][N:30]([CH3:44])[C:31](=[CH:32][CH:33]=[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:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[S:56]

Komponenten

7

Edukt 4

HCID 97312Acetic acid, (phenylthio)-, ethyl esterHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioateHCID 131716212N(3-dimethylamino-3-t-butyloxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 178418339Butyllithium

Produkt 1

HCID 1317162116-Ethyl 1-tert-butyl 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-t-butyloxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (4.05 g), a 1.6M solution (8.8 cc) of butyllithium in hexane and ethyl (phenylthio)acetate (2.8 g) in tetrahydrofuran (65 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, 6-ethyl 1-tert-butyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate (2.6 g), m.p. 85°-88° C., is obtained.

Aufarbeitung

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c8c762a8393540459b15feb7cd32495a
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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