Potassium Carbonate → 4-Ethyl-5-[4-(trifluoromethyl)phenyl]oxazole

HRID 1672572노트

반응식

HRID 1672572 반응식
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[N+:13]([CH:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:16][CH3:17])#[C-:14].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:16]([C:15]1[N:13]=[CH:14][O:8][C:7]=1[C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=1)[CH3:17]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

생성물 1

HCID 666965954-Ethyl-5-[4-(trifluoromethyl)phenyl]oxazole수율 88.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 4-(trifluoromethyl)benzaldehyde (3.60 mL, 27.0 mmol), 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (6.02 g, 27.0 mmol), and K2CO3 (4.47 g, 32.4 mmol) in MeOH (100 mL) was heated to reflux. After 1.5 hr the reaction mixture was cooled to ambient temperature, and the volatiles evaporated at reduced pressure. The residue was partitioned between Et2O (100 mL) and H2O (100 mL). The separated aqueous phase was extracted with Et2O. The combined organic extract was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. Chromatography on silica gel (Analogix® Intelliflash 280™; SF40-150 g column; 10% to 30% EtOAc/hexanes eluant, 30 min) afforded 5.75 g (88%) of the title compound as a pale yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.90-7.78 (m, 4H), 2.79 (q, J=7.5, 2H), 1.23 (t, J=7.5, 3H). MS (DCI+) m/z 242 (M+H).

후처리

  1. temperaturewas heated to reflux
  2. customthe volatiles evaporated at reduced pressure
  3. customThe residue was partitioned between Et2O (100 mL) and H2O (100 mL)
  4. extractionThe separated aqueous phase was extracted with Et2O
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d05a13115b46489fa8f87cfcdcb3824e
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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