Pyridine → 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime

HRID 1059670노트

반응식

HRID 1059670 반응식
[C:1]1([CH3:11])[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[CH:26]=[C:25]2[C:20]([C:21](=[N:28][OH:29])[CH:22]([CH3:27])[CH2:23][O:24]2)=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH3:11])[C:2]([S:7]([O:29][N:28]=[C:21]2[C:20]3[C:25](=[CH:26][C:17]([C:13]4[O:12][CH:16]=[CH:15][CH:14]=4)=[CH:18][CH:19]=3)[O:24][CH2:23][CH:22]2[CH3:27])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 8623o-Toluenesulfonyl chlorideHCID 73868111HCID 73868111, 화합물

생성물 1

HCID 865864777-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime수율 57.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Toluenesulfonyl chloride (397 mg, 2.08 mmol) was added to a 0° C. solution of 7-furyl-3-methyl-4-chromanone oxime (61) (461 mg, 1.89 mmol) and pyridine (0.5 mL) in CH2Cl2 (10 mL). After 6 hours, the mixture was diluted with CH2Cl2 (30 mL) and washed with 59 HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified via flash chromatography using 5:1 hexanes:EtOAc as the eluent, to provide 7-furyl-3-methyl-4-chromanone O-(toluenesulfonyl)-oxime (62) (429 mg) as a pink solid, m.p. 163-164° C. (dec).

후처리

  1. washwashed with 59 HCl (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography

출처 및 근거

ORD 기록
ord-74bc0f9d401c43f09f1c547d4dd0a731
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521622B1

반응 노트

불러오는 중…