1-Phenyl-1-propanone → 1,2-Diphenylpropan-1-one

HRID 13902

반응식

HRID 13902 반응식
CC(C)([O-])C.[Na+].O1CCCC1.Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH2:20][CH3:21]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC([B-](C2C=CC(C)=CC=2)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O>[C:23]1([C:19](=[O:22])[CH:20]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

8

반응물 4

HCID 71481-Phenyl-1-propanoneHCID 7964ChlorobenzeneHCID 8028TetrahydrofuranHCID 23676156Sodium t-butoxide

생성물 1

HCID 2385181,2-Diphenylpropan-1-one수율 77%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 23136639Tri-tert-butylphosphonium tetra-para-tolylborate촉매HCID 962Water용매

실험 절차

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.022 g (0.1 mmol) of palladium (II) acetate, 0.721 g (7.5 mmol) of sodium-tert-butoxide and 5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.058 g (0.1 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 22° C. for 30 minutes. 0.563 g (5 mmol) of chlorobenzene was added, followed by stirring at 22° C. for 30 minutes. 0.738 g (5.5 mmol) of propiophenone was added, followed by stirring at 70° C. for 6 hours. After the completion of the reaction, 2.5 ml of water was added, followed by separation. The organic phase was purified by column chromatography to afford 0.810 g of 1,2-diphenyl-1-propanone (yield: 77 mol % based on chlorobenzene). The identification of the product was made by mass spectroscopy, 1H-NMR and 13C-NMR.

후처리

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 22° C. for 30 minutes
  5. stirringby stirring at 22° C. for 30 minutes
  6. stirringby stirring at 70° C. for 6 hours
  7. additionwas added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

출처 및 근거

ORD 기록
ord-991c6d13caaa4528976beb0f2ec2d241
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728176B2

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