Water → HCID 18670800、化合物

HRID 1059107ノート

反応式

HRID 1059107 の反応式
C([O:3][C:4]([C:6]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:21])[NH:8][CH:7]=1)=[O:5])C.C(OC(=O)C=CC1C2C(=CC=CC=2)C=CC=1)C.CC(C)([O-])C.[K+].O>O1CCCC1>[OH:5][C:4]([C:6]1[C:10]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[C:9]([CH3:21])[NH:8][CH:7]=1)=[O:3]

参加物

6

反応物 4

HCID 962WaterHCID 18670784HCID 18670784、化合物HCID 23665647Potassium tert-butoxideHCID 53428571Ethyl 3-(naphthalen-1-yl)prop-2-enoate

生成物 1

HCID 18670800HCID 18670800、化合物収率 66.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

3-ethoxycarbonyl-5-methyl-4-(naphthalen-1-yl)-1H-pyrrole 4.3 g(18.9 mmol) of 3-(naphthalen-1-yl)-acrylic acid ethylester prepared in Preparation 6-1) and 3.95 g(18.9 mmol) of α-methyltosylmethylisocyanide disclosed in A. M. van Leusen, et al., Tetrahedron Letter, 1975, 40, 3487 were dissolved in 100 ml of tetrahydrofuran. 2.55 g(22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran was slowly added thereto, which was then refluxed for 30 minutes. To the reaction solution was added 100 ml of water to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethylether, washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography using a solvent mixture of ethyl acetate/n-hexane(1/3, v/v) as an eluent to give 3.50 g(12.5 mmol, Yield 66%) of the title compound.

後処理

  1. additionwas slowly added
  2. temperaturewhich was then refluxed for 30 minutes
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. extractionThe residue was extracted with diethylether
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. additiona solvent mixture of ethyl acetate/n-hexane(1/3

出典と根拠

ORDレコード
ord-0bf3e081ee7f49e493a1ec9fd7b75ab5
出典データセット
uspto-grants-2003_02
特許番号
US06518429B2

反応ノート

読み込み中…