Potassium Carbonate → (E)-3-(3'-Adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester

HRID 41726

반응식

HRID 41726 반응식
[C:1]([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:39]([O:42][C:43](=[O:47])[O:44][CH2:45]I)[CH2:40][CH3:41]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:1]([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:45][O:44][C:43]([O:42][CH2:39][CH2:40][CH3:41])=[O:47])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 11042958Iodomethyl 2-(methyl)ethyl carbonateHCID 86660473HCID 86660473, 화합물

생성물 1

HCID 67426176(E)-3-(3'-Adamantan-1-yl-4'-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of (E)-3-(3′-adamantan-1yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester (250 mg, 0.581 mmol) and K2CO3 (241 mg, 1.74 mmol) in water (2.9 ml) was stirred at RT for 30 min. Tetrabutylammonium hydrogen sulfate (197 mg, 0.581 mmol) and DCM (1.4 ml) were then added and the stirring maintained for further 10 min. A solution of carbonic acid iodomethyl ester propyl ester (184 mg, 0.755 mmol) in DCM (1.4 ml) was then added dropwise. The biphasic solution was stirred overnight at RT. After standard work-up and removal of the solvent under reduced pressure, the residue was taken up in Et2O. Tetrabutylammonium iodide was filtered off and the solvent was evaporated. (E)-3-(3′-Adamantan-1-yl-4′-propoxycarbonyloxymethoxy-biphenyl-4-yl)acrylic acid tert-butyl ester was obtained (117 mg, 36%) after purification on silica gel (EtOAc/hexane 12:88).

후처리

  1. temperaturethe stirring maintained for further 10 min
  2. stirringThe biphasic solution was stirred overnight at RT
  3. customAfter standard work-up and removal of the solvent under reduced pressure
  4. filtrationTetrabutylammonium iodide was filtered off
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-b52aefb45520443ca761841de668ff7c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530517B2

연결된 노트

불러오는 중…