Tetrahydrofuran → Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

HRID 612565ノート

反応式

HRID 612565 の反応式
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]1COCC1.C[Mg]I.[NH4+].[Cl-]>CCOCC>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:19]=[CH:18][C:10]([C:11]([OH:12])([CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 80389Ethyl 4-phenylbenzoylformateHCID 178418373HCID 178418373、化合物

生成物 1

HCID 21184093Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-25 °C

実験手順

To a flame dried 500 mL flask flushed with N2, was added 24 g (100 mmol) of ethyl 4-phenylbenzoylformate and 300 mL of anhydrous THF. The solution was cooled with stirring to -25° C. and 37 mL (110 mmol) of a 3.0 M solution of methylmagnesium iodide was added at a rate to maintain the reaction temperature below -10° C. The reaction progress was monitored by TLC and upon disappearance of starting material, 100 mL of saturated NH4Cl solution and 200 mL of ether were added. The organic layer was separated and washed with 2×50 mL of brine, dried (MgSO4) and concentrated leaving racemic ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate as an oil.

後処理

  1. customTo a flame dried 500 mL flask
  2. customflushed with N2
  3. temperatureThe solution was cooled
  4. temperatureto maintain the reaction temperature below -10° C
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with 2×50 mL of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe9e8562776d45cc960830e972f3134a
出典データセット
uspto-grants-1999_12
特許番号
US06005000

反応ノート

読み込み中…