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

HRID 641242노트

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HRID 641242 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b290eed7e44846aa9960f0bb315394a7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696196B2

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