Trichloroacetyl chloride → Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate

HRID 520383

반응식

HRID 520383 반응식
[C:1]([O:6][CH3:7])(=[O:5])[CH2:2][CH:3]=[CH2:4].[Cl:8][C:9]([Cl:14])(Cl)[C:10](Cl)=[O:11]>COCCOC.CCOCC.[Cu].[Zn]>[Cl:8][C:9]1([Cl:14])[C:10](=[O:11])[CH2:4][CH:3]1[CH2:2][C:1]([O:6][CH3:7])=[O:5]

참가 물질

6

반응물 2

HCID 6420Trichloroacetyl chlorideHCID 77314Methyl 3-butenoate

생성물 1

HCID 57686758Methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate수율 47.4%

시약·촉매·용매 3

HCID 10290809Zinc copper couple촉매HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a reaction mixture of methyl but-3-enoate (1.0 g, 10 mmol) and zinc-copper couple (2.0 g, 15.5 mmol) in DME (5 mL) and ether (30 mL) was added trichloroacetyl chloride (2.98 mL, 26.7 mmol) under N2 at rt. The reaction mixture was stirred at rt for 2.5 days. The reaction mixture was filtrated through diatomaceous earth (Celite®) and washed with DCM. The filtrate was concentrated and purified by 80 g silica gel cartridge which was eluted with a 20 min gradient of 0-60% EtOAc in hexane to yield methyl 2-(2,2-dichloro-3-oxocyclobutyl)acetate (1.0 g). 1H NMR (400 MHz, CDCl3) ppm 3.66-3.70 (3H, m), 3.42-3.55 (1H, m), 3.23-3.39 (1H, m), 3.05 (1H, dd, J=17.82, 8.78 Hz), 2.90 (1H, dd, J=16.94, 6.65 Hz), 2.67 (1H, dd, J=16.94, 8.16 Hz).

후처리

  1. filtrationThe reaction mixture was filtrated through diatomaceous earth (Celite®)
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated
  4. custompurified by 80 g silica gel cartridge which
  5. washwas eluted with a 20 min gradient of 0-60% EtOAc in hexane

출처 및 근거

ORD 기록
ord-728029bb49324341b6175dd63544f003
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326973B2

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