Phthalic Anhydride → 2-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

HRID 57185

反応式

HRID 57185 の反応式
[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].NC(N)=[O:23].OO.C1(=O)OC(=O)C2=CC=CC=C12.[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][N+:14]=2[O-:23])[CH:10]=[CH:11][CH:12]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 5

HCID 6811Phthalic Anhydride2 回HCID 10340Sodium CarbonateHCID 24437Sodium Sulfite2 回HCID 31294Carbamide PeroxideHCID 57516851tert-Butyl 3-(3-methylpyridin-2-yl)benzoate

生成物 1

HCID 584883712-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

tert-Butyl-3-(3-methylpyridin-2-yl)benzoate (1.0 eq) is dissolved in EtOAc (6 vol). Water (0.3 vol) is added followed by urea-hydrogen peroxide (3 eq). The phthalic anhydride (3 eq) is added portion-wise as a solid to maintain the temperature in the reactor below 45° C. After completion of phthalic anhydride addition, the mixture is heated to 45° C. After stirring for an additional 4 hours, the heat is turned off 10% w/w aqueous Na2SO3 (1.5 eq) is added via addition funnel. After completion of Na2SO3 addition, the mixture is stirred for an additional 30 minutes and the layers separated. The organic layer is stirred and 10% w/w aq. Na2CO3 (2 eq) is added. After stirring for 30 minutes, the layers are allowed to separate. The organic phase is washed 13% w/v aq NaCl. The organic phase is then filtered and concentrated to afford crude 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (95%) that is used directly in the next step.

後処理

  1. temperatureto maintain the temperature in the reactor below 45° C
  2. additionis added via addition funnel
  3. stirringthe mixture is stirred for an additional 30 minutes
  4. customthe layers separated
  5. stirringThe organic layer is stirred
  6. stirringAfter stirring for 30 minutes
  7. customto separate
  8. washThe organic phase is washed 13%
  9. filtrationThe organic phase is then filtered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-54f1f4a5a4234998848d3dffeb94c269
出典データセット
uspto-grants-2016_09
特許番号
US09434717B2

関連ノート

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