Hexane → 2-Benzoyl-benzoic acid N',N'-dimethyl-hydrazide

HRID 44434

反応式

HRID 44434 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][N:10]([CH3:22])[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].CCCCCC>C1COCC1>[CH3:22][N:10]([CH3:9])[NH:11][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:12](=[O:21])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8058HexaneHCID 2489762-(Dimethylamino)isoindoline-1,3-dioneHCID 178418255HCID 178418255、化合物

生成物 1

HCID 90925702-Benzoyl-benzoic acid N',N'-dimethyl-hydrazide収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

A solution of phenylmagnesium bromide in THF (11.6 mmol) was slowly added to a solution of phthalimide 16 (10.5 mmol) in THF (110 ml) at −78 ° C. and stirred under argon for 15 minutes. The mixture was then progressively warmed to −30 ° C. for 1 hour. The reaction was quenched with a saturated aqueous solution of NH4Cl (15 ml) and the aqueous layer extracted with Et2O. The combined organic layers were washed with brine (20 ml), dried over MgSO4 and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography with (1:2) EtOAc:hexane, to give 80% yield of the desired product.

後処理

  1. customThe reaction was quenched with a saturated aqueous solution of NH4Cl (15 ml)
  2. extractionthe aqueous layer extracted with Et2O
  3. washThe combined organic layers were washed with brine (20 ml)
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting crude product was purified by silica gel chromatography with (1:2) EtOAc

出典と根拠

ORDレコード
ord-3976c3e264b3492f8f54258f8d544731
出典データセット
uspto-grants-2013_09
特許番号
US08541428B2

関連ノート

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