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

HRID 733181

反応式

HRID 733181 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-89951e2fd3ce4e01a09824d7d1d6ead2
出典データセット
uspto-grants-2009_09
特許番号
US07589095B2

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