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

HRID 1397357노트

반응식

HRID 1397357 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3410745a38b74038bca80b3501b13daf
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

반응 노트

불러오는 중…