Toluene → Methyl 3-benzoylcinnamate

HRID 59604

반응식

HRID 59604 반응식
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].C(N(CC)CC)C.C1(C)C=CC=CC=1.[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>[C:5]([C:4]1[CH:3]=[C:2]([CH:15]=[CH:14][CH:13]=1)[CH:32]=[CH:31][C:30]([O:34][CH3:35])=[O:33])(=[O:6])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 7294Methyl Acrylate2회HCID 8471Triethylamine2회HCID 705483-Bromobenzophenone

생성물 1

HCID 68514943Methyl 3-benzoylcinnamate수율 91%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매2회HCID 167845palladium(II) acetate촉매2회HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 3-bromobenzophenone (5.0 g, 19 mmol), palladium acetate (215 mg, 0.958 mmol), and tri-o-tolylphosphine (290 mg, 0.953 mmol) was added triethylamine (3.3 mL, 45 mmol), toluene (4 mL), and methyl acrylate (2.2 mL, 27 mmol). The mixture was heated at 100° C. for 18 hours at which time TLC analysis showed the reaction was still incomplete. Additional portions of palladium acetate (215 mg, 0.958 mmol), tri-o-tolylphosphine (290 mg, 0.953 mmol), triethylamine (3.3 mL, 45 mmol) and methyl acrylate (2.2 mL, 27 mmol) were added, and the mixture was heated at 110° for a further 18 hours. After cooling to room temperature the mixture was poured into water and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed sequentially with water and brine, and then dried (MgSO4) and concentrated to a brown oil (5.3 g). The oil was chromatographed over silica gel. Elution with ethyl acetate/hexanes (1:9) afforded methyl 3-benzoylcinnamate (4.6 g, 91%) as a yellow solid.

후처리

  1. temperaturethe mixture was heated at 110° for a further 18 hours
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic extracts were washed sequentially with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a brown oil (5.3 g)
  7. customThe oil was chromatographed over silica gel
  8. washElution with ethyl acetate/hexanes (1:9)

출처 및 근거

ORD 기록
ord-002532044fab40899f91945612940698
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440926B2

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