Tert-butyl acetoacetate → Methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate

HRID 46541

反応式

HRID 46541 の反応式
[F-].[K+].[CH3:3][O:4][CH:5]([O:12][CH3:13])/[CH:6]=[CH:7]\[C:8]([O:10][CH3:11])=[O:9].[C:14]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17]>C(O)(C)(C)C>[C:21]([O:20][C:14]([CH:15]([C:16](=[O:17])[CH3:18])[CH:6]([CH:5]([O:12][CH3:13])[O:4][CH3:3])[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:19])([CH3:24])([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 15538Tert-butyl acetoacetateHCID 522689Potassium FluorideHCID 12283105methyl (2Z)-4,4-dimethoxy-2-butenoate

生成物 1

HCID 20396638Methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

Into a 500-ml reactor are placed 40 g of potassium fluoride, 40 ml of dry tert-butanol, 123 g of methyl cis-4,4-dimethoxy-2-butenate and 36 g of tert-butyl acetoacetate. The mixture is heated at 100° C. with stirring on an oil bath for two days. On completion of the reaction, the tert-butanol is distilled off from the mixture. The residue is dissolved in ethyl acetate, and the solution washed with an aqueous solution of common salt and then dried. The solvent is removed from the product. The resulting residue is purified by a silica gel column and distilled at reduced pressure, giving methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate (compound (5), R1 =t-Bu, R2 =R3 =CH3) in a yield of 95.4%, b.p. 72°-76° C./0.014 mm Hg.

後処理

  1. customInto a 500-ml reactor are placed
  2. customOn completion of the reaction
  3. distillationthe tert-butanol is distilled off from the mixture
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe solution washed with an aqueous solution of common salt
  6. customdried
  7. customThe solvent is removed from the product
  8. customThe resulting residue is purified by a silica gel column
  9. distillationdistilled at reduced pressure

出典と根拠

ORDレコード
ord-6ea2e3098a98444b92423b26c3fe1be2
出典データセット
uspto-grants-1979_11
特許番号
US04173707

関連ノート

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