Methyl morpholine oxide → Methyl 7-formyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

HRID 1506391노트

반응식

HRID 1506391 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[O:11][N:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]=1[CH2:7][CH2:6]2)=C.C[N+]1([O-])CC[O:24]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.[Os](=O)(=O)(=O)=O.O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[O:11][N:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]=1[CH2:7][CH2:6]2)=[O:24]

참가 물질

8

반응물 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 68182163Methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

생성물 1

HCID 86669891Methyl 7-formyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

시약·촉매·용매 4

HCID 962Water촉매HCID 962Water용매3회HCID 8028Tetrahydrofuran용매HCID 30318Osmium Tetroxide용매

실험 절차

To a clear solution of methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate (Preparation 45B, 65 mg, 0.255 mmol) in THF (4 mL) were sequentially added N-methylmorpholine-N-oxide in water (0.084 mL, 0.407 mmol) and osmium tetroxide in water (0.062 mL, 10.19 μmol) at room temperature. The solution was stirred vigorously at room temperature overnight. Sodium periodate (109 mg, 0.509 mmol) in water (1 mL) was added and the mixture was stirred at room temperature under nitrogen for two hours. Water (2 mL) was then added and the mixture was concentrated to remove THF. The resulting solid was filtered, washed with water (2×2 mL), and dried to give 72 mg of product as a yellow solid. The compound had an HPLC ret. time=0.88/2.0 min. (condition E).

후처리

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature under nitrogen for two hours
  3. concentrationthe mixture was concentrated
  4. customto remove THF
  5. filtrationThe resulting solid was filtered
  6. washwashed with water (2×2 mL)
  7. customdried

출처 및 근거

ORD 기록
ord-13d1023f6b47497cb8d04771b130973f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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