Methyl 4-methoxyacetoacetate → HCID 178496271、化合物

HRID 1407164ノート

反応式

HRID 1407164 の反応式
[F:1][C:2]1([F:16])[O:7][C:6]2[CH:8]=[C:9]([F:13])[C:10]([NH2:12])=[CH:11][C:5]=2[O:4][C:3]1([F:15])[F:14].[N:17]([O-])=O.[Na+].[CH3:21][O:22][CH2:23][C:24](=[O:30])[CH2:25][C:26]([O:28][CH3:29])=[O:27].CC([O-])=O.[Na+]>Cl.O.CCO>[CH3:21][O:22][CH2:23][C:24](=[O:30])[C:25](=[N:17][NH:12][C:10]1[C:9]([F:13])=[CH:8][C:6]2[O:7][C:2]([F:1])([F:16])[C:3]([F:15])([F:14])[O:4][C:5]=2[CH:11]=1)[C:26]([O:28][CH3:29])=[O:27]

参加物

8

反応物 4

HCID 123500Methyl 4-methoxyacetoacetateHCID 517045Sodium AcetateHCID 144057012,2,3,3,7-Pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amineHCID 23668193Sodium Nitrite

生成物 1

HCID 178496271HCID 178496271、化合物収率 85%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 2,2,3,3,7-pentafluoro-2,3-dihydro-1,4-benzodioxin-6-amine (4.87 g, 20.2 mmol) in 6 M HCl aqueous solution (20.2 mL) was added a solution of NaNO2 (1.67 g, 24.2 mmol) in water (4 mL) at 0° C. The mixture was stirred at 0° C. for 15 min. To a suspension of methyl 4-methoxy-3-oxobutanoate (2.61 mL, 20.2 mmol) and NaOAc (30.3 g) in EtOH (34 mL) was added the above solution at 0° C. The mixture was stirred at 0° C. for 15 min. The precipitates were collected by filtration, washed with water, dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and concentrated in vacuo to yield the title compound (6.84 g, 85% yield) as a red solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.33 (3H, s), 3.82 (3H, s), 4.68 (2H, s), 7.66-7.93 (2H, m), 12.16 (1H, brs).

後処理

  1. additionwas added the above solution at 0° C
  2. stirringThe mixture was stirred at 0° C. for 15 min
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. dissolutiondissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c574079ccad545f9a49ac694fcc8463d
出典データセット
uspto-grants-2014_12
特許番号
US08916566B2

反応ノート

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