Sodium hydride → Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate

HRID 390606

反応式

HRID 390606 の反応式
[H-].[Na+].[CH3:3][CH2:4][CH:5](P(OCC)(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:19][NH:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:19][NH:20][C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[C:5](\[CH2:4][CH3:3])/[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 13945243'-Methylaminobiphenyl-4-carbaldehyde

生成物 1

HCID 68962496Ethyl 2-[1-(3'-methylaminobiphenyl-4-yl)meth-(e)-ylidene]butyrate収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

197 mg (4.9 mmol) of sodium hydride are added to a mixture of 1.2 mL (4.9 mmol) of triethyl 2-phosphonobutyrate and 415 mg of 3′-methylaminobiphenyl-4-carbaldehyde (2.0 mmol) in 10 mL of tetrahydrofuran. The reaction mixture is stirred at room temperature overnight, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the residue (1.1 g) is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 438 mg (72%) of ethyl 2-[1-(3′-methylaminobiphenyl-4-yl)meth-(E)-ylidene]butyrate are obtained in the form of off-white crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe residue (1.1 g) is purified by chromatography on a column of silica
  6. washeluted with a 90/10 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-919b2e7b34d54fd6b60e8686154cb1ac
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

関連ノート

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