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Sodium hydride → 3-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester

HRID 1245394
ノート
印刷プレビュー

反応式

HRID 1245394 の反応式
COP([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(OC)=O.[H-].[Na+].[CH3:17][C:18]1[CH:27]=[C:26]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH2:40][CH:39]([CH:41]=O)[O:38][N:37]=3)=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>CN(C=O)C>[C:11]([O:10][C:8](=[O:9])[CH:7]=[CH:41][CH:39]1[O:38][N:37]=[C:36]([C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:28][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([CH3:17])[CH:27]=3)=[CH:31][CH:32]=2)[CH2:40]1)([CH3:12])([CH3:13])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 218980783-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde

生成物 1

HCID 696396783-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester収率 61.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

t-Butyl dimethylphosphonoacetate (0.31 g, 1.38 mmol) was added to a suspension of sodium hydride (washed with hexanes) (0.061 g @60%, 1.5 mmol) in DMF (3 mL) cooled in an ice bath, under a nitrogen atmosphere. The reaction was stirred for 0.5 h and the product from step 10b (0.31 g, 1.38 mmol) in DMF (3 mL) was added. The reaction was stirred for 2 h at 0° C. and was complete. This was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting methylene chloride:ethyl acetate (70:30) to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester (0.38 g, 61%) as an oil. MS found: (M+H)+=445.

後処理

  1. temperaturecooled in an ice bath, under a nitrogen atmosphere
  2. stirringThe reaction was stirred for 2 h at 0° C.
  3. customThis was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe product was purified by FCC on silica gel
  9. washeluting methylene chloride:ethyl acetate (70:30)

出典と根拠

ORDレコード
ord-e5ae2a6712374c82a15a87da5b33719f
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07125870B2

反応ノート

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