alpha-Naphthaleneacetic acid, ethyl ester → Diethyl 2-dimethylamino-5-(1-naphthyl)-2,4-hexadienedioate

HRID 477348

反応式

HRID 477348 の反応式
CN(C)C(=CC=C(C1C=CC=CC=1)C(OCC)=O)C(OCC)=S.F[B-](F)(F)F.[CH3:29][N:30]([CH3:42])[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:33]=[N+](C)C.CC[O-].[Na+].[C:47]1([CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59])[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:50]=[CH:49][CH:48]=1>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:57]([C:47]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:50]=[CH:49][CH:48]=1)[C:58]([O:60][CH2:61][CH3:62])=[O:59])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

参加物

6

反応物 4

HCID 62428alpha-Naphthaleneacetic acid, ethyl esterHCID 2723922Sodium ethoxideHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

生成物 1

HCID 53994139Diethyl 2-dimethylamino-5-(1-naphthyl)-2,4-hexadienedioate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 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (10 g), a 2M ethanolic solution of sodium ethylate (26 cc) and ethyl 2-(1-naphthyl)acetate (7.5 g) in ethanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume), diethyl 2-dimethylamino-5-(1-naphthyl)-2,4-hexadienedioate (2.2 g) is obtained in the form of a yellow oil, and is used in the crude state in the subsequent syntheses.

後処理

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

出典と根拠

ORDレコード
ord-680d84392e4040ff89533067cd470af4
出典データセット
uspto-grants-1989_12
特許番号
US04886835

関連ノート

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