Hydrochloric Acid → 1-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

HRID 625258ノート

反応式

HRID 625258 の反応式
[C:1]1([CH2:7][CH2:8][Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][N:23]=1)[C:15](N(OC)C)=[O:16].C1([Mg]Cl)C=CC=CC=1.Cl.[OH-].[Na+]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([C:15](=[O:16])[CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:21]=[CH:22][N:23]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 448186542-Bromo-N-methoxy-N-methylisonicotinamideHCID 178418865HCID 178418865、化合物HCID 178478979HCID 178478979、化合物

生成物 1

HCID 867059361-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
25 °C

実験手順

1.0 mL of 1.0 N phenyethylmagnesium chloride in THF was added dropwise to a −78° C. solution of 200 mg of 2-bromo-N-methoxy-N-methylisonicotinamide in 6 mL of THF. The solution was allowed to warm to 25° C. After 10 minutes the solution was cooled back to −78° C. and an additional 1.0 mL of 1.0 N phenylmagnesium chloride in THF was added. The mixture was warmed to 25° C. and after 10 minutes 10 mL of 1.0 N hydrochloric acid was added. The solution was then made basic with excess aqueous sodium hydroxide solution and the mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate and the combined organic extracts were dried over sodium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel to give 168 mg of product.

後処理

  1. temperatureAfter 10 minutes the solution was cooled back to −78° C.
  2. additionwas added
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washThe aqueous phase was washed with ethyl acetate
  5. dry with materialthe combined organic extracts were dried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-99ab9ee0dc904f49a4db7e86153fdc96
出典データセット
uspto-grants-2016_04
特許番号
US09301951B2

反応ノート

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