N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamide → HCID 21193738, 화합물

HRID 582133

반응식

HRID 582133 반응식
CON(C)[C:4](=[O:21])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1.[CH3:23][Li]>O1CCCC1.Cl.CO>[CH:16]1([O:15][C:9]2[CH:8]=[C:7](/[CH:6]=[CH:5]/[C:4](=[O:21])[CH3:23])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

참가 물질

6

반응물 2

HCID 54075299N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamideHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 21193738HCID 21193738, 화합물수율 97%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamide (1.986 g, 6.50 mmol) in dry tetrahydrofuran (15 ml) at -78° C. was added methyl lithium (1.4M solution in hexanes, 10.20 ml, 14.3 mmol) dropwise over 3 minutes. The resulting solution was stirred for 1 hour at 0° C., after which time the reaction mixture was diluted with 5% HCl in methanol (20 ml) at 0° C., and partitioned between brine (35 ml) and an equal volume of methylene chloride and diethyl ether (100 ml). The organics were dried (Na2SO4) and concentrated in vacuo to give a light yellow oil. The oil was purified by flash chromatography (SiO2 ; ethyl acetate/hexane (35:65)) to afford the title compound as a colorless oil (1.642 g).

후처리

  1. custompartitioned between brine (35 ml)
  2. dry with materialThe organics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a light yellow oil
  5. customThe oil was purified by flash chromatography (SiO2 ; ethyl acetate/hexane (35:65))

출처 및 근거

ORD 기록
ord-04ec3b1e33d446ce8d1f98da301597c4
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922751

연결된 노트

불러오는 중…