Tri-o-tolylphosphine → Methyl 2-acetylamino-3-(4-benzyloxy-3,5-dimethyl-phenyl)-acrylate

HRID 641242ノート

反応式

HRID 641242 の反応式
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([NH:21][C:22](=[CH2:27])[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]([NH:21][C:22](=[CH:27][C:12]1[CH:13]=[C:14]([CH3:15])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH3:17])[CH:11]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:20])[CH3:19]

参加物

7

反応物 3

HCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

生成物 1

HCID 67273532Methyl 2-acetylamino-3-(4-benzyloxy-3,5-dimethyl-phenyl)-acrylate

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen atmosphere a mixture of 40.0 g (137 mmol) 2-benzyloxy-5-bromo-1,3-dimethylbenzene and 24.1 g (165 mmol) methyl 2-acetylamino-acrylate in 420 mL triethylamine and 200 mL acetonitrile was combined with 3.5 g (11.2 mmol) tri-o-tolyl-phosphane and 2.5 g (11.1 mmol) Pd(OAc)2 and the mixture was stirred for 18 h at 80° C. The precipitate was suction filtered, the filtrate was evaporated down i. vac. and combined with 800 mL DCM and 800 mL water. The organic phase was separated off, suction filtered through Na2SO4, the solvent was removed i.vac., the residue was stirred with EtOAc, suction filtered and dried i. vac.

後処理

  1. filtrationfiltered
  2. customthe filtrate was evaporated down i
  3. customThe organic phase was separated off
  4. filtrationsuction filtered through Na2SO4
  5. customthe solvent was removed i.vac
  6. stirring, the residue was stirred with EtOAc, suction
  7. filtrationfiltered
  8. customdried i

出典と根拠

ORDレコード
ord-b290eed7e44846aa9960f0bb315394a7
出典データセット
uspto-grants-2010_04
特許番号
US07696196B2

反応ノート

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