Hydrochloric Acid → HCID 178418663、化合物

HRID 5259

反応式

HRID 5259 の反応式
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]=[CH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](O)=[O:44])=[CH:30][CH:29]=1.Cl>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:3][C:2]1[CH2:4][O:5][C:6](=[O:7])[C:1]=1[C:43](=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=[CH:34][C:31]1[CH:30]=[CH:29][C:28]([Cl:27])=[CH:33][CH:32]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521261Tetronic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5440741310-(4-Chlorophenyl)dec-9-enoic acid

生成物 1

HCID 178418663HCID 178418663、化合物収率 58.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirring solution of 189 mg (1.89 mmol) of tetronic acid in 15 mL of dimethylformamide is added 290 μL (2.08 mmol) of triethylamine and 8 mg (66 μmol) of 4-dimethylaminopyridine at 0° C. Next, 427 mg (2.22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 690 mg (2.20 mmol) of 10-(4-chlorophenyl)dec-9-enoic acid as a mixture of E and Z isomers are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ethyl acetate. The combined organic layers are washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified via flash chromatography on a 40 mm×150 mm silica gel column eluting with 5% methanol/ethyl acetate to give 400 mg (58%) of pure 4-hydroxy-3-[10-(4-chlorophenyl)-1-oxodec-9-enyl] -2(5H)-furanone as a mixture of E and Z isomers.

後処理

  1. additionare added
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via flash chromatography on a 40 mm×150 mm silica gel column
  7. washeluting with 5% methanol/ethyl acetate

出典と根拠

ORDレコード
ord-bdf94d64f6764381bbbb7b18839e7b85
出典データセット
uspto-grants-1993_09
特許番号
US05242945

関連ノート

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