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

HRID 1672572ノート

反応式

HRID 1672572 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d05a13115b46489fa8f87cfcdcb3824e
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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