Sodium hydride → HCID 9924161、化合物

HRID 2114630ノート

反応式

HRID 2114630 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14].[CH3:21][O:22][CH2:23][CH2:24]Br.[H][H]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[O:7][C:8]1[C:12]([CH2:13][CH3:14])=[N:11][N:10]([CH2:24][CH2:23][O:22][CH3:21])[C:9]=1[CH2:15][CH3:16]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 9878953HCID 9878953、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 9924161HCID 9924161、化合物収率 58.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% dispersion in oil, 34 mg, 0.850 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole of Example 3 (200 mg, 0.701 mmol) and methoxyethyl bromide (117 mg, 0.850 mmol) in dry N,N-dimethylformamide (2ml) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 45 minutes during which time hydrogen was evolved and the yellow solution turned dark brown. The reaction mixture was quenched by the addition of water (5 ml) and the mixture concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 ml) and washed with water (10 ml) and brine (10 ml) and then dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a brown oil. The crude product was purified by flash column chromatography on silica gel eluting with pentane:diethyl ether (80:20, by volume) to provide the title compound (140 mg) as a colourless oil.

後処理

  1. customThe reaction mixture was quenched by the addition of water (5 ml)
  2. concentrationthe mixture concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  4. washwashed with water (10 ml) and brine (10 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a brown oil
  9. customThe crude product was purified by flash column chromatography on silica gel eluting with pentane:diethyl ether (80:20, by volume)

出典と根拠

ORDレコード
ord-2301399813364d0ba1a5212f403470d0
出典データセット
uspto-grants-2008_10
特許番号
US07435728B2

反応ノート

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