Triphenylphosphine → (2-(4-Fluorophenyl)oxazol-4-YL)methanamine

HRID 1397357ノート

反応式

HRID 1397357 の反応式
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:8][CH:9]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]2[O:8][CH:9]=[C:5]([CH2:4][NH2:1])[N:6]=2)=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 613736504-(Azidomethyl)-2-(4-fluorophenyl)oxazole

生成物 1

HCID 28287570(2-(4-Fluorophenyl)oxazol-4-YL)methanamine収率 75%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

A solution of 4-(azidomethyl)-2-(4-fluorophenyl)oxazole (0.5 g, 2.3 mmol) in THF—H2O (15 mL, 8:2 v/v) was cooled to 0° C. and triphenylphosphine (892 mg, 3.4 mmol) was added. The reaction mixture was allowed to warm up to room temperature and then stirred for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was diluted with 1.5N HCl. The aqueous layer was washed with CH2Cl2 and then the pH of the aqueous layer was adjusted to ˜8-9 using 10% NaOH solution. The organic product was extracted with CH2Cl2 and organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford (2-(4-fluorophenyl)oxazol-4-yl)methanamine (330 mg, yield 75%) as a pale yellow liquid, which was carried through without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.01-7.98 (m, 2H), 7.94 (s, 1H), 7.38-7.34 (m, 2H), 3.65 (d, J=1.1 Hz, 2H). MS (ESI) m/z: Calculated for C10H9FN2O: 192.07. found: 193.2 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with 1.5N HCl
  3. washThe aqueous layer was washed with CH2Cl2
  4. extractionThe organic product was extracted with CH2Cl2 and organic layer
  5. washwas washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3410745a38b74038bca80b3501b13daf
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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