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

HRID 460293ノート

反応式

HRID 460293 の反応式
[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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f19ed56a81fd4efdadef39c40b868554
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

反応ノート

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