Hydrochloric Acid → Ethyl 3-oxo-3-(thiophen-3-yl)propanoate

HRID 21570

반응식

HRID 21570 반응식
C(NC1CCCCC1)(C)C.[Li]CCCC.[S:16]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17]1.Cl.[CH3:25][CH2:26][O:27][C:28]([CH3:30])=[O:29]>C1COCC1.[Cl-].[Na+].O>[O:22]=[C:21]([C:18]1[CH:19]=[CH:20][S:16][CH:17]=1)[CH2:30][C:28]([O:27][CH2:26][CH3:25])=[O:29]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2회HCID 62386CyclohexylisopropylamineHCID 27763773-Thenoyl chlorideHCID 178418339Butyllithium

생성물 1

HCID 10535956Ethyl 3-oxo-3-(thiophen-3-yl)propanoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of N-isopropylcyclohexylamine (5.64 g) in THF (80 mL) cooled to -78° C. under nitrogen was added nBuLi (25 mL, 1.6M in hexane) and the mixture was stirred for 30 min. EtOAc (1.95 mL) was added and after a further 30 min., 3-thiophene carbonyl chloride (from Step 1) dissolved in 3 mL THF was added. After 30 min., 1N HCl (75 mL) was added followed by brine and EtOAc. The organic layer was separated, dried and concentrated. Purification by column chromatography (5% EtOAc/hexane) afforded the title compound as an oil.

후처리

  1. additionwas added
  2. waitAfter 30 min.
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customPurification by column chromatography (5% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-3fafb40f159e43c99b50e87fa2e6886b
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424320

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