Potassium Iodide → ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoate

HRID 322879

反応式

HRID 322879 の反応式
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])=[O:3].Cl[CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[O:18][CH:20]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:3])[CH3:1]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

生成物 1

HCID 23204307ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoate収率 34.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-benzyloxy-2-hydroxyaceto-phenone (1.2 g), ethyl (RS)-4-chloro-4-phenyl-butanoate (1.21 g), potassium carbonate (760 mg), potassium iodide (35 mg) and dimethylformamide (30 mL) is stirred at 100° C. for 8 hours. It is evaporated to dryness and the resulting residue is partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer is dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography of the resulting oil, eluting with 15-30% ethyl acetate/hexane, affords ethyl (RS)-4-(2-acetyl-5-benzyloxy-phenoxy)-4-phenylbutanoate (0.73 g), in the form of a yellow oil.

後処理

  1. customIt is evaporated to dryness
  2. customthe resulting residue is partitioned between ethyl acetate (200 mL) and water (200 mL)
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography of the resulting oil, eluting with 15-30% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-38a7180b845244e4becca23853d94f6e
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

関連ノート

読み込み中…