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

HRID 46541
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HRID 46541 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ea2e3098a98444b92423b26c3fe1be2
출처 데이터셋
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04173707

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