Potassium Carbonate → 5-(4-Bromophenyl)-4-ethyloxazole

HRID 1672580ノート

反応式

HRID 1672580 の反応式
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:4][CH3:5])#[C-:2].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]2[O:22][CH:2]=[N:1][C:3]=2[CH2:4][CH3:5])=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

生成物 1

HCID 666967705-(4-Bromophenyl)-4-ethyloxazole

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (1.21 g, 5.40 mmol), 4-bromobenzaldehyde (1 g, 5 mmol), and K2CO3 (0.896 g, 6.49 mmol) in MeOH (27 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and the solvent was evaporated at reduced pressure. The residue was partitioned between water and EtOAc. The separated organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was dissolved in minimal toluene, loaded on silica gel, and eluted with 2 column volumes of hexane, then 10% to 50% EtOAc/hexanes. The result was 1.27 g (93%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.84 (s, 1H), 7.60-7.54 (m, 2H), 7.49-7.43 (m, 2H), 2.78 (q, J=7.5, 2H), 1.32 (t, J=7.6, 3H). MS (DCI+) m/z 252/254 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe solvent was evaporated at reduced pressure
  4. customThe residue was partitioned between water and EtOAc
  5. washThe separated organic phase was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in minimal toluene
  10. washeluted with 2 column volumes of hexane

出典と根拠

ORDレコード
ord-98617a6edcb845ed8394373b6afe3cb2
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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