Dicyclohexylcarbodiimide → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]cyclopropane-carboxylate

HRID 1995168노트

반응식

HRID 1995168 반응식
C1(O)CCC1.[CH3:6][C:7]1([CH3:24])[CH:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18]CC2)=[O:13])[CH:8]1[C:21]([OH:23])=[O:22].[CH3:25][C:26]1(C)[CH:28](/C=C\C(O)=O)[CH:27]1C([O-])=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:24][C:7]1([CH3:6])[C@@H:9](/[CH:10]=[CH:11]\[C:12]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18]2)=[O:13])[C@H:8]1[C:21]([O:23][C:26]([CH3:28])([CH3:27])[CH3:25])=[O:22]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 76218CyclobutanolHCID 705231322,2-dimethyl-3-[Z-2-(cyclohexyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acidHCID 867390082,2-dimethyl-3-[Z-2-carboxy-ethenyl]-cyclopropane-carboxylate

생성물 1

HCID 86739007tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]cyclopropane-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

1.7 ml of cyclobutanol were added to a solution of 4 g of tert.-butyl (1R, cis) 2,2-dimethyl-3-[Z-2-carboxy-ethenyl]-cyclopropane-carboxylate in 20 ml of methylene chloride and 3.45 g of dicyclohexylcarbodiimide and a solution of 28 mg of 4-dimethylamino-pyridine in 20 ml of methylene chloride were added thereto at 0° to 5° C. with stirring. The mixture was stirred for 2 hours at 5° C. and 2 hours at room temperature and was then filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 9-1 n-hexane-isopropyl ether mixture yielded 2.3 g of tert.-butyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclobutoxycarbonyl)-ethenyl]-cyclopropane-carboxylate.

후처리

  1. stirringThe mixture was stirred for 2 hours at 5° C. and 2 hours at room temperature
  2. filtrationwas then filtered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 9-1 n-hexane-isopropyl ether mixture

출처 및 근거

ORD 기록
ord-cf8599a175474c7a81b7998b038b93e1
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04402972

반응 노트

불러오는 중…