Hydrochloric Acid → HCID 19369950、化合物

HRID 849227

反応式

HRID 849227 の反応式
[I-].[Sm+2].[I-].O=O.[CH3:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)=[O:8].[C:19](OC)(=[O:22])[CH:20]=C.Cl.O1CCC[CH2:27]1>C(O)(C)(C)C>[CH3:18][O:17][C:11]1[CH:10]=[C:9]([C:7]2([CH3:27])[O:8][C:19](=[O:22])[CH2:20][CH2:6]2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

参加物

8

反応物 6

HCID 313Hydrochloric AcidHCID 977OxygenHCID 7294Methyl AcrylateHCID 8028Tetrahydrofuran2 回HCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 178506586HCID 178506586、化合物

生成物 1

HCID 19369950HCID 19369950、化合物

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

100 ml of a 0.1 M solution of samarium(II) iodide in tetrahydrofuran is mixed, with oxygen carefully excluded, with the solution of 710 mg of 3,4-dimethoxyacetophenone, 500 mg of methyl acrylate and 350 mg of tert-butanol in 5 ml of tetrahydrofuran. The reaction solution is mixed thoroughly, allowed to stand for two hours at room temperature and then poured into 100 ml of 20% hydrochloric acid. It is stirred for two hours at room temperature and extracted with diethyl ether. The ether phase is washed with sodium thiosulfate solution and water, dried on sodium sulfate and concentrated by evaporation in a vacuum. The oily residue is chromatographed on a silica gel column (Kromasil 100/10 μm) with a hexane-tert-butyl methyl ether mixture (4:1). 570 mg of (R,S)-5-(3,4-dimethoxyphenyl)-5-methyl-dihydro-2-furanone is eluted, melting point 71.2° C.

後処理

  1. additionThe reaction solution is mixed thoroughly
  2. extractionextracted with diethyl ether
  3. washThe ether phase is washed with sodium thiosulfate solution and water
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe oily residue is chromatographed on a silica gel column (Kromasil 100/10 μm) with a hexane-tert-butyl methyl ether mixture (4:1)
  7. wash570 mg of (R,S)-5-(3,4-dimethoxyphenyl)-5-methyl-dihydro-2-furanone is eluted

出典と根拠

ORDレコード
ord-2f2a8f24c2ce48d2844e84f48e2d08ed
出典データセット
uspto-grants-2000_01
特許番号
US06011060

関連ノート

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