Diethyl Oxalate → Methyl 4-(4-methylphenyl)-2,4-dioxobutanoate

HRID 878550

反応式

HRID 878550 の反応式
[Na].C(O[C:5](=[O:11])[C:6]([O:8][CH2:9]C)=[O:7])C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1>CO.CC(OC)(C)C>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH2:20][C:5](=[O:11])[C:6]([O:8][CH3:9])=[O:7])=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 7268Diethyl OxalateHCID 8500p-METHYLACETOPHENONEHCID 5360545Sodium

生成物 1

HCID 308119Methyl 4-(4-methylphenyl)-2,4-dioxobutanoate収率 48.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 15413tert-Butyl methyl ether溶媒2 回

実験手順

Sodium (1.0 g, 43 mmol) was dissolved in MeOH (50 mL) and then evaporated to a dry white powder. To the powder was added MTBE (100 mL) and diethyloxalate (5.14 g, 35.2 mmol). To the resulting solution was added a solution of 1-(4-methylphenyl)ethanone (5.0 g, 37.3 mmol) in MTBE (50 mL) dropwise over 45 min. The resulting suspension was allowed to stir for 1 h, and the precipitate was filtered and washed with MTBE/hexanes (1:1, 50 mL). The solid was suspended in 1 N HCl (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were dried (MgSO4), filtered, and concentrated to an oily residue which crystallized on standing at rt. The yellow solid was triturated with MTBE/hexanes (1:1) and filtered to give the title compound (3.76 g, 46%) as a white solid.

後処理

  1. customevaporated to a dry white powder
  2. filtrationthe precipitate was filtered
  3. washwashed with MTBE/hexanes (1:1, 50 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oily residue which
  8. customcrystallized
  9. customon standing at rt
  10. customThe yellow solid was triturated with MTBE/hexanes (1:1)
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-ea916c09d6f94aebbef9b14e61b9f23b
出典データセット
uspto-grants-2015_03
特許番号
US08987461B2

関連ノート

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