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

HRID 1672580노트

반응식

HRID 1672580 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-98617a6edcb845ed8394373b6afe3cb2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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