Ethyl Acetate → Ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

HRID 7677

反応式

HRID 7677 の反応式
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([C:24]([O:26][CH2:27][CH3:28])=[O:25])#N.CCOC(C)=O>C1COCC1.O>[CH2:27]([O:26][C:24]([CH:8]1[C:7](=[O:10])[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9]1)=[O:25])[CH3:28]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 69336Ethyl cyanoformateHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 559688Ethyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

1,4-Cyclohexanedione mono-ethylene ketal (25 g) was dissolved in THF and cooled to −78° C. 1.0 M Lithium bis(trimethylsily)amide (160 mL) in THF was added dropwise. After 30 min, ethyl cyanoformate (15.9 mL) was added dropwise. After 60 min, the solution was poured into EtOAc and water containing ice. The organic layer was washed with water and brine before it was dried and concentrated. This crude was filtered through a plug of silica to give the 8-oxo-1,4-dioxa-spiro[4.5]decane-7-carboxylic acid ethyl ester (32.4 g). MS found: (M+H)+=228.9.

後処理

  1. waitAfter 60 min
  2. additioncontaining ice
  3. washThe organic layer was washed with water and brine before it
  4. customwas dried
  5. concentrationconcentrated
  6. filtrationThis crude was filtered through a plug of silica

出典と根拠

ORDレコード
ord-93b60822344942a1918edaf6b1b87f2d
出典データセット
uspto-grants-2006_08
特許番号
US07087604B2

関連ノート

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