Phenethyl bromide → Ethyl 3-oxo-2-(2-phenylethyl)butanoate

HRID 483015

反応式

HRID 483015 の反応式
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C[O-].[Na+].[CH2:13](Br)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:15]1([CH2:14][CH2:13][CH:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7666Phenethyl bromideHCID 8868Ethyl AcetoacetateHCID 10942334Sodium Methoxide

生成物 1

HCID 219459Ethyl 3-oxo-2-(2-phenylethyl)butanoate収率 91.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Ethyl acetoacetate (53.8 g., 0.29 mole) was dissolved in 110 ml. of anhydrous ethanol. Sodium methoxide (17.3 g., 0.36 mole) was added portionwise to the stirred solution, allowing the temperature to rise to 40°-50°. The mixture was then heated to reflux (80°-82°) and phenethyl bromide (53.8 g., 0.32 mole) added dropwise over 1 hour. Reflux was continued for 20 hours. The reaction mixture was cooled to 30°-35° and filtered over diatomaceous earth with ethanol wash. The combined filtrate and wash were concentrated in vacuo to a pot temperature of 50°, cooled to 25°, diluted with 150 ml. of hexane and 40 ml. of water, acidified to pH 6.5-7.0 with 6N HCl. The hexane layer was separated and washed with 25 ml. of fresh water. The aqueous layer were combined and back-washed with 40 ml. of fresh hexane. The hexane layers were combined, washed with 60 ml. of water, dried over 15 g. MgSO4, filtered and evaporated to yield title product as an oil (62 g., 91%).

後処理

  1. customto rise to 40°-50°
  2. temperatureThe mixture was then heated
  3. additionadded dropwise over 1 hour
  4. temperatureReflux
  5. temperatureThe reaction mixture was cooled to 30°-35°
  6. filtrationfiltered over diatomaceous earth with ethanol
  7. washwash
  8. washThe combined filtrate and wash
  9. concentrationwere concentrated in vacuo to a pot temperature of 50°
  10. temperaturecooled to 25°
  11. additiondiluted with 150 ml
  12. customThe hexane layer was separated
  13. washwashed with 25 ml
  14. washback-washed with 40 ml
  15. washwashed with 60 ml
  16. dry with materialof water, dried over 15 g
  17. filtrationMgSO4, filtered
  18. customevaporated

出典と根拠

ORDレコード
ord-273244fa72cc45449396d994d0ae100d
出典データセット
uspto-grants-1986_03
特許番号
US04576964

関連ノート

読み込み中…