Ammonium Chloride → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

HRID 465559ノート

反応式

HRID 465559 の反応式
[Cl-].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:3]=1.CC(C)([O-])C.[K+].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH2:56][CH:57]=O)[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:34][C:35]1[CH:36]=[CH:37][C:38]([S:41]([NH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH:49]([CH2:56][CH:57]=[CH:8][C:4]2[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=2)[CH2:50][CH2:51][C:52]([O:54][CH3:55])=[O:53])(=[O:43])=[O:42])=[CH:39][CH:40]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 10340312Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoateHCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 54073742Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a suspension of 0.545 g of 3-pyridylmethyltriphenylphosphonium chloride in 6 ml tetrahydrofuran is added slowly 1.6 ml of 1.61M potassium t-butoxide in tetrahydrofuran and the mixture is stirred at room temperature for 1 h. A solution of 0.454 g of methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)-octanoate in 1 ml tetrahydrofuran is added slowly and then stirred for 18 h at room temperature. The reaction mixture is poured into saturated ammonium chloride and extracted with ethyl acetate (3×15 ml). The combined organic extracts are dried, filtered and evaporated to give a dark residue which is purified by flash chromatography to obtain, as a light amber oil, methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]-octanoate. The product is a mixture of cis and trans isomers, the major component being the cis isomer. The above product is dissolved in 5 ml methylene chloride in a crystallizing dish and the solution is irradiated for 5 h under UV light. The organic layer is diluted with methylene chloride and washed with aqueous sodium thiosulfate. The organic phase is dried, filtered and evaporated. The residue is purified by preparative thin layer chromatography to obtain a clear oil identified as about a 1:1 mixture of cis and trans isomers.

後処理

  1. stirringstirred for 18 h at room temperature
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. customThe combined organic extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customto give a dark residue which
  7. customis purified by flash chromatography

出典と根拠

ORDレコード
ord-979116d94d9c42f180ca70732d3d1090
出典データセット
uspto-grants-1992_10
特許番号
US05153214

反応ノート

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