N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamide → HCID 21193738、化合物

HRID 582133

反応式

HRID 582133 の反応式
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

参加物

6

反応物 2

HCID 54075299N-methoxy-N-methyl-3-(3-cyclopentyloxy-4-methoxyphenyl)prop-2-enamideHCID 178418348HCID 178418348、化合物

生成物 1

HCID 21193738HCID 21193738、化合物収率 97%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-04ec3b1e33d446ce8d1f98da301597c4
出典データセット
uspto-grants-1999_07
特許番号
US05922751

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