Methyl Acetate → Methyl 4-(3',5'-dimethylphenyl)acetoacetate

HRID 2109498

反応式

HRID 2109498 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:5](OC)=O.[H-].[Na+].[C:15]([O:18][CH3:19])(=[O:17])[CH3:16].[CH3:20][O:21]CCOC>>[CH3:12][C:10]1[CH:9]=[C:4]([CH2:5][C:20](=[O:21])[CH2:16][C:15]([O:18][CH3:19])=[O:17])[CH:3]=[C:2]([CH3:1])[CH:11]=1

参加物

5

反応物 4

HCID 6584Methyl AcetateHCID 80711,2-Dimethoxyethane3 回HCID 24758Sodium hydrideHCID 32786Benzoic acid, 3,5-dimethyl-, methyl ester

生成物 1

HCID 69048054Methyl 4-(3',5'-dimethylphenyl)acetoacetate収率 50%

実験手順

A solution of methyl 3,5-dimethylbenzoate (50 g; 300 mmol) in DME (80 ml) was added to a suspension of NaH (26.8 g; 60% in oil; 670 mmol) in DME (80 ml) under argon. The mixture was heated to reflux and a solution of methyl acetate (45 g; 610 mmol) in DME (40 ml) added dropwise. The mixture was heated for a further 4 h under reflux. The mixture was cooled and the excess of NaH destroyed by the dropwise addition of MeOH (40 ml). The mixture was poured into dilute HCl (2N), extracted with Et2O and the organic phase was washed with water, brine and dried over MgSO4. The residue was purified by flash chromatography eluting with Et2O/hexanes (10% Et2O) to give methyl 4-(3′,5′-dimethylphenyl)acetoacetate as a yellow oil (31 g).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated for a further 4 h
  4. temperatureunder reflux
  5. temperatureThe mixture was cooled
  6. customthe excess of NaH destroyed by the dropwise addition of MeOH (40 ml)
  7. additionThe mixture was poured into dilute HCl (2N)
  8. extractionextracted with Et2O
  9. washthe organic phase was washed with water, brine
  10. dry with materialdried over MgSO4
  11. customThe residue was purified by flash chromatography
  12. washeluting with Et2O/hexanes (10% Et2O)

出典と根拠

ORDレコード
ord-66aeef61a52d464f9a68758c894876b4
出典データセット
uspto-grants-2009_04
特許番号
US07514570B2

関連ノート

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