Potassium Carbonate → 3-(3,3-Dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde

HRID 460293노트

반응식

HRID 460293 반응식
[CH3:1][C:2]1([CH3:24])[C:6]2[CH:7]=[C:8]([C:20](=[O:23])[CH2:21][CH3:22])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[C:5]=2[O:4][CH2:3]1.Br[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][C:35]([F:38])([F:37])[F:36])[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][C:2]1([CH3:1])[C:6]2[CH:7]=[C:8]([C:20](=[O:23])[CH2:21][CH3:22])[CH:9]=[C:10]([C:32]3[CH:31]=[C:28]([CH:27]=[CH:26][C:33]=3[O:34][C:35]([F:36])([F:37])[F:38])[CH:29]=[O:30])[C:5]=2[O:4][CH2:3]1

참가 물질

9

반응물 3

HCID 11430Potassium CarbonateHCID 131504163-Bromo-4-(trifluoromethoxy)benzaldehydeHCID 184453891-[3,3-Dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-propan-1-one

생성물 1

HCID 184453993-(3,3-Dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde수율 73.6%

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-[3,3-dimethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-5-yl]-propan-1-one (1.33 g, 4.05 mmol), 3-bromo-4-trifluoromethoxybenzaldehyde (example 1h) (1.09 g, 4.05 mmol) and potassium carbonate (1.12 g, 8.10 mmol) in toluene (12 mL), ethanol (2.4 mL) and water (1.5 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (234 mg, 0.20 mmol) was added and the mixture heated at reflux under argon for 19 hrs. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 1.17 g of 3-(3,3-dimethyl-5-propionyl-2,3-dihydro-benzofuran-7-yl)-4-trifluoromethoxy-benzaldehyde (50%). 1H NMR (300 MHz; CDCl3): 1.23 (t, J=7.2 Hz, 3H), 1.42 (s, 6H), 2.99 (q, J=7.2 Hz, 2H), 4.34 (s, 2H), 7.52 (dd, J1=7.2 Hz, J2=1.8 Hz, 1H), 7.84 (d, J=2.1 Hz, 1H), 7.85 (d, J=2.13 Hz, 1H), 7.96 (dd, J1=8.4 Hz, J2=2.1 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 10.05 (s, 1H).

후처리

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 19 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-f19ed56a81fd4efdadef39c40b868554
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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