Hydrochloric Acid → Ethyl 2-[1-(3-ethoxy-4-hydroxyphenyl)meth-(e)-ylidene]butyrate

HRID 390656ノート

反応式

HRID 390656 の反応式
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[OH:30])[CH:25]=O)[CH3:20].[Cl-].[NH4+].Cl>O1CCCC1>[CH2:19]([O:21][C:22]1[CH:23]=[C:24](/[CH:25]=[C:3](\[CH2:2][CH3:1])/[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:27]=[CH:28][C:29]=1[OH:30])[CH3:20]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8467EthylvanillinHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoate

生成物 1

HCID 68957248Ethyl 2-[1-(3-ethoxy-4-hydroxyphenyl)meth-(e)-ylidene]butyrate収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 11.8 g (46 mmol) of triethyl 2-phosphonobutyrate in 20 mL of tetrahydrofuran is added to a mixture of 1.8 g (46 mmol) of sodium hydride in 20 mL of tetrahydrofuran at 0° C. The reaction medium is stirred for 15 minutes. A solution of 3.4 g (20 mmol) of 3-ethoxy-4-hydroxybenzaldehyde prepared as in Example 32a in 20 mL of tetrahydrofuran is then added to the reaction mixture and the reaction medium is stirred at room temperature for 3 days. The reaction medium is then poured into saturated ammonium chloride solution, acidified with aqueous 2 N hydrochloric acid 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 (12.5 g) is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 3.7 g (71%) of ethyl 2-[1-(3-ethoxy-4-hydroxyphenyl)meth-(E)-ylidene]butyrate are obtained in the form of a yellow oil.

後処理

  1. additionis then added to the reaction mixture
  2. stirringthe reaction medium is stirred at room temperature for 3 days
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated off
  7. customthe residue (12.5 g) is purified by chromatography on a column of silica
  8. washeluted with an 80/20 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-a085885f2af64434acb1367abb06df80
出典データセット
uspto-grants-2013_02
特許番号
US08383652B2

反応ノート

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