Dimethylformamide → 4-(4-Chlorophenoxy)-2-propylbenzaldehyde

HRID 1172817

반응식

HRID 1172817 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH2:21][CH2:22][CH3:23])(=O)=O.C([SiH](CCCCCCCC)CCCCCCCC)CCCCCCC.C(N(CC)CC)C.C1(PC2C=CC=CC=2)C=CC=CC=1.CN([CH:74]=[O:75])C>C(OCC)(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([CH:74]=[O:75])=[C:8]([CH2:21][CH2:22][CH3:23])[CH:9]=2)=[CH:15][CH:16]=1

참가 물질

9

반응물 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70017DiphenylphosphineHCID 87780Trioctylsilane, 95%HCID 574201394-(4-Chlorophenoxy)-2-propylphenyl trifluoromethanesulfonate

생성물 1

HCID 574201434-(4-Chlorophenoxy)-2-propylbenzaldehyde

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of the triflate from Step 6 of Example 1 (3.98 g, 10 mmol), trioctylsilane (6.7 mL, 15 mmol), triethyl amine (7.0 mL, 25 mmol), palladium acetate (0.22 g, 0.5 mmol) and diphenylphosphine (0.21 g, 0.5 mmol) in DMF (60 mL) was stirred at 80° C. under an atmosphere of carbon monoxide (50 psi) for 5 h. The reaction was then diluted with ethyl acetate and water. The organic layer was washed with water and concentrated. The residue was purified by chromatography on silica gel to give the title product.

후처리

  1. washThe organic layer was washed with water
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-3b6927da955b4e40becf93811e4e50c6
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834036B2

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