Triethylamine → Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

HRID 1176234ノート

反応式

HRID 1176234 の反応式
Cl[CH:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[CH2:22](N(CC)CC)[CH3:23]>O1CCCC1>[CH2:22]([C:6]1[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([CH:3]=[CH:2][C:18]([O:20][CH3:21])=[O:19])[CH:14]=[CH:13][C:7]=1[C:8]([OH:10])=[O:9])[CH3:23]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 15091479Ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate

生成物 1

HCID 68501280Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The solution of 3.20 g of ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate in 130 ml of tetrahydrofuran is admixed with 6.46 ml of triethylamine and stirred at reflux over 18 hours. The reaction mixture is cooled, poured onto water (300 ml) and extracted with tert-butyl methyl ether (2×300 ml). The organic phases are washed successively with water (2×300 ml) and brine (150 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The crude title compound is obtained as a slightly yellowish solid from the residue. Rf=0.30 (1:2 EtOAc-heptane). Rt=4.50.

後処理

  1. temperatureat reflux over 18 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (300 ml)
  4. extractionextracted with tert-butyl methyl ether (2×300 ml)
  5. washThe organic phases are washed successively with water (2×300 ml) and brine (150 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-12e4507a435949b3a1266462ab8bc8c7
出典データセット
uspto-grants-2010_11
特許番号
US07842688B2

反応ノート

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