Sodium ethoxide → Ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate

HRID 477328

反応式

HRID 477328 の反応式
C1(C(=O)C(SC)=CC=C(N(C)C)C(OCC)=O)C=CC=CC=1.F[B-](F)(F)F.[CH3:28][N:29]([CH3:41])[C:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=[N+](C)C.CC[O-].[Na+].[CH3:46][S:47][CH2:48][C:49]([C:51]1[CH:52]=[C:53]([OH:58])[C:54](=[CH:56][CH:57]=1)[OH:55])=[O:50]>C(O)C>[OH:58][C:53]1[CH:52]=[C:51]([C:49](=[O:50])[C:48]([S:47][CH3:46])=[CH:32][CH:31]=[C:30]([N:29]([CH3:41])[CH3:28])[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:57]=[CH:56][C:54]=1[OH:55]

参加物

6

反応物 4

HCID 2723922Sodium ethoxideHCID 137183393',4'-Dihydroxy-2-(methylthio)acetophenoneHCID 44325574Ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino2,4-hexadienoateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

生成物 1

HCID 53865515Ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate収率 17.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (60 cc) and 4-[2-(methylthio)acetyl]pyrocatechol (7.9 g) in ethanol (60 cc). After purification on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, ethyl 6-(3,4-dihydroxyphenyl)-2-dimethylamino-5-methylthio-6-oxo-2,4-hexadienoate (2.4 g), m.p. 144° C., is obtained.

後処理

  1. customAfter purification on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

出典と根拠

ORDレコード
ord-0b9009d9704d420ea5d4e8232a849219
出典データセット
uspto-grants-1989_12
特許番号
US04886835

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