Hydrochloric Acid → 2-(1-Hydroxaminoethyl)phenoxathiin

HRID 1087380

反応式

HRID 1087380 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 156610132-(1-Hydroxaminoethyl)phenoxathiin収率 89.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e653b95f47a446148c1ae41f2403e257
出典データセット
uspto-grants-1991_07
特許番号
US05036067

関連ノート

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