Hydrochloric Acid → 2-(1-Hydroxaminoethyl)phenoxathiin

HRID 1087380

반응식

HRID 1087380 반응식
[N:1](=[C:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=1)[CH3:4])[OH:2].B.N1C=CC=CC=1.Cl>C(O)C>[NH:1]([CH:3]([C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=1)[CH3:4])[OH:2]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 5151822-(1-Hydroximinoethyl)phenoxathiinHCID 2723995Borane;pyridine

생성물 1

HCID 156610132-(1-Hydroxaminoethyl)phenoxathiin수율 89.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

The oxime from Step 1 (450 mg, 1.75 mmol) was suspended in ethanol (9 mL) and, at 0° C., there was added pyridine-borane (325 mg, 3.5 mmol) and 4M ethanolic hydrogen chloride (HCl) (1.33 mL, 5.32 mmol). The mixture was stirred at 0° C. for 20 minutes, then at room temperature for 1 hour. The ethanol was evaporated and the residue partitioned between water and ether. The aqueous portion was basified with 1N aqueous sodium hydroxide and extracted twice with ether. Drying of the ether and evaporation afforded the title product (408 mg) as an oil which slowly became a white solid, m.p.: 64°-67° C.

후처리

  1. waitat room temperature for 1 hour
  2. customThe ethanol was evaporated
  3. customthe residue partitioned between water and ether
  4. extractionextracted twice with ether
  5. dry with materialDrying of the ether and evaporation

출처 및 근거

ORD 기록
ord-e653b95f47a446148c1ae41f2403e257
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05036067

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