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Triethylamine → 2-[3-(Benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole

HRID 1740287
ノート
印刷プレビュー

反応式

HRID 1740287 の反応式
FC(F)(F)S(O[C:7]1[C:12]2[CH:13]=[CH:14][O:15][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:18][C:19]1([CH3:33])[CH2:23][O:22][C:21]([C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)=[N:20]1.C(N(CC)CC)C>CN(C)C=O>[O:15]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([C:26]3[CH:25]=[C:24]([C:21]4[O:22][CH2:23][C:19]([CH3:33])([CH3:18])[N:20]=4)[CH:29]=[CH:28][CH:27]=3)[C:12]=2[CH:13]=[CH:14]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 218381293-(4,4-Dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyboraneHCID 21838291Benzofuran-4-yl trifluoromethanesulfonate

生成物 1

HCID 218382442-[3-(Benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole収率 69.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-trifluoromethylsulfonyloxy-benzofuran (2 g), 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyldihydroxyborane (2.14 g), tetrakis(triphenyl-phosphine)palladium(0) (0.26 g) and triethylamine (2.28 g) in N,N-dimethylformamide (40 ml) was heated at 85° C. for 3 hours under nitrogen atmosphere. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was successively washed with 10% sodium carbonate aqueous solution, brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with toluene. The fractions containing the desired products were collected and evaporated in vacuo to afford 2-[3-(benzofuran-4-yl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.52 g).

後処理

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml)
  3. washThe organic layer was successively washed with 10% sodium carbonate aqueous solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with toluene
  7. additionThe fractions containing the desired products
  8. customwere collected
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-1800dacb4d7b48099001b521ef37f276
出典データセット
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05968985

反応ノート

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