Methyl phenylacetate → HCID 67917566、化合物

HRID 1885798ノート

反応式

HRID 1885798 の反応式
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:14](=O)([O-])[O-:15].[Na+].[Na+]>C(OC)=O.CN(C=O)C>[OH:15][CH:14]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9]

参加物

6

反応物 3

HCID 7559Methyl phenylacetateHCID 10340Sodium CarbonateHCID 24758Sodium hydride

生成物 1

HCID 67917566HCID 67917566、化合物収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 7865Methyl formate溶媒

反応条件

温度
-5 °C

実験手順

A solution of methyl phenylacetate (16.03g) in methyl formate (132ml) and dry DMF (100 ml) was added dropwise over 40 minutes to a stirred suspension of sodium hydride (5.14g) in dry DMF (200ml) at between 0° and 5° C. (effervescence and foaming). The resulting mixture was stirred at about -5° C. for 30 minutes, diluted with dry DMF (250ml), then allowed to warm and stir at room temperature for 3 hours. Ice and sodium carbonate were added to the mixture and it was washed with ether (x2), then acidified with concentrated hydrochloric acid and extracted with ether (x4). The extracts were washed with water (x3), treated with magnesium sulphate and charcoal, filtered and concentrated to give methyl 3-hydroxy-2-phenylpropenoate (13.56g, 71%) as a solid, m.p. 33.5°-35.5° C., which was used for the subsequent steps without further purification.

後処理

  1. temperatureto warm
  2. stirringstir at room temperature for 3 hours
  3. washwas washed with ether (x2)
  4. extractionextracted with ether (x4)
  5. washThe extracts were washed with water (x3)
  6. additiontreated with magnesium sulphate and charcoal
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-9a8b399dc2cc4d2ca863a9031732fc22
出典データセット
uspto-grants-1992_09
特許番号
US05145954

反応ノート

読み込み中…