2,2-Dimethyl-1,3-dioxane-4,6-dione → Ethyl 6-(benzyloxy)-3-oxohexanoate

HRID 733181

반응식

HRID 733181 반응식
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1(C)[O:23]C(=O)[CH2:20][C:18](=O)[O:17]1.CN(C1C=CC=CN=1)C.ClC(OC(C)=C)=O.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl>[CH2:18]([O:17][C:16](=[O:23])[CH2:15][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:20]

참가 물질

7

반응물 5

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 218852-DimethylaminopyridineHCID 93846Isopropenyl chloroformateHCID 516920Potassium bisulfateHCID 5622014-(Benzyloxy)butanoic acid

생성물 1

HCID 10264779Ethyl 6-(benzyloxy)-3-oxohexanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

4-Benzyloxybutyric acid (6.38 mL), Meldrum's acid (5.76 g) and dimethylaminopyridine (9.77 g) were dissolved in DCM (200 mL) and cooled to 0° C. A solution of isopropenyl chloroformate in dichloromethane (100 mL) was added dropwise and stirring at 0° C. continued for a further 2 h. Potassium hydrogen sulphate (200 mL of a 10% aqueous solution) was then added, the organic phase separated, dried over sodium sulphate, and evaporated under reduced pressure. The residue was dissolved in ethanol (200 mL) and heated at reflux overnight. Following cooling, the solvent was evaporated under reduced pressure and the resultant oil was purified by flash silica column chromatography. 6-Benzyloxy-3-oxo-hexanoic acid ethyl ester was isolated as an orange oil (8.53 g).

후처리

  1. customthe organic phase separated
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethanol (200 mL)
  5. temperatureheated
  6. temperatureat reflux overnight
  7. temperatureFollowing cooling
  8. customthe solvent was evaporated under reduced pressure
  9. customthe resultant oil was purified by flash silica column chromatography

출처 및 근거

ORD 기록
ord-89951e2fd3ce4e01a09824d7d1d6ead2
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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