Pyridine → HCID 13193764、化合物

HRID 1285546ノート

反応式

HRID 1285546 の反応式
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13](C)=[C:14]([C:27]([O:29][CH3:30])=[O:28])[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18].N1C=CC=CC=1>C(O)C.C(Cl)(Cl)Cl>[CH3:10][C:11]1[NH:12][C:13]2[CH2:30][O:29][C:27](=[O:28])[C:14]=2[CH:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]=1[C:17]([O:19][CH3:20])=[O:18]

参加物

5

反応物 2

HCID 1049PyridineHCID 129839Dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate

生成物 1

HCID 13193764HCID 13193764、化合物収率 63%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

1.58 grams of 80 percent pyridinium bromide perbromide (3.95 millimoles) was added in one portion to a cooled to 0° C. solution of 1.00 gram (3.32 millimoles) of dimethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.4 milliliter of pyridine in 20 milliliters of dry ethanol-free chloroform. The resulting mixture was stirred for 45 minutes at 0° C. and then heated at reflux temperature for 1.3 hous. Thereafter, the mixture was cooled to room temperature, diluted with chloroform and the resulting solution washed successively with 2N hydrochloric acid and brine, dried over magnesium sulfate, and dried solution filtered to remove the drying agent, and then subjected to reduce pressure to vaporize the solvent and to recover as residue 1.41 grams of product as a yellow oil. The oil was chromatographed on silica gel using 70 percent ethyl acetate--30 percent hexane as eluant to obtain 595 milligrams (63 percent yield) of purified methyl 2-methyl-4-phenyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]-pyridine-3-carboxylate product which after recrystallization from ethyl acetate-hexane and drying at 60° C. at 0.005 millimeters mercury pressure for 17 hours had a melting point of 193°-196° C. Elemental analyses for the product were as follows:

後処理

  1. temperatureheated
  2. temperatureat reflux temperature for 1.3 hous
  3. temperatureThereafter, the mixture was cooled to room temperature
  4. washthe resulting solution washed successively with 2N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate, and dried solution
  6. filtrationfiltered
  7. customto remove the drying agent
  8. customto recover as residue 1.41 grams of product as a yellow oil
  9. customThe oil was chromatographed on silica gel using 70 percent ethyl acetate--30 percent hexane as eluant

出典と根拠

ORDレコード
ord-d24751920ecc4ab0b1594719c281d0e0
出典データセット
uspto-grants-1986_01
特許番号
US04567268

反応ノート

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