Ethyl Acetate → Ethyl 3-oxo-3-(oxolan-3-yl)propanoate

HRID 1020773

반응식

HRID 1020773 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:14][CH2:15][CH3:16])(=[O:13])[CH3:12].C[O:18][C:19]([CH:21]1[CH2:25][CH2:24][O:23][CH2:22]1)=O>C1COCC1>[CH2:15]([O:14][C:11](=[O:13])[CH2:12][C:19](=[O:18])[CH:21]1[CH2:25][CH2:24][O:23][CH2:22]1)[CH3:16]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 10678263Methyl oxolane-3-carboxylate

생성물 1

HCID 22831881Ethyl 3-oxo-3-(oxolan-3-yl)propanoate수율 38.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of lithium bis(trimethylsilyl)amide (1 M in hexanes; 100 mL) in THF (200 mL) at −78° C. was added dry ethyl acetate (10.8 g, 12 mL, 122.5 mmol) dropwise. After 30 min at −78° C., the mixture was treated with a solution of tetrahydro-furan-3-carboxylic acid methyl ester (6.0 g, 46.1 mmol) in THF (50 mL). After 4 h at −78° C., the reaction was quenched with satd. aq. NH4Cl, warmed to rt, and extracted with EtOAc (5×75 mL). The combined organic layers were washed with satd. aq. NaCl, dried, and concentrated to give a colorless oil. Chromatography on SiO2 (EtOAc/CH2Cl2) afforded the title compound (3.3 g).

후처리

  1. waitAfter 4 h at −78° C.
  2. customthe reaction was quenched with satd
  3. extractionextracted with EtOAc (5×75 mL)
  4. washThe combined organic layers were washed with satd
  5. dry with materialaq. NaCl, dried
  6. concentrationconcentrated
  7. customto give a colorless oil

출처 및 근거

ORD 기록
ord-d8e878b4c7114f8eb8f1c400ff797d4f
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716475B2

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