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

HRID 1506391ノート

反応式

HRID 1506391 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water触媒HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒HCID 30318Osmium Tetroxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13d1023f6b47497cb8d04771b130973f
出典データセット
uspto-grants-2015_12
特許番号
US09216972B2

反応ノート

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