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

HRID 351365

반응식

HRID 351365 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

1,4-Cyclohexanedione mono-ethylene ketal (25 g) was dissolved in THF and cooled to −78° C. 1M 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

후처리

  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

출처 및 근거

ORD 기록
ord-61d7887e28344bd297d6736670177602
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183270B2

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