Dimethyl Sulfoxide → Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate

HRID 453514ノート

反応式

HRID 453514 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[OH:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>O.CCOC(C)=O>[C:14]([O:13][C:11](=[O:12])[CH2:10][C:5]1[CH:6]=[CH:7][C:8]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)=[C:3]([C:1]#[N:2])[CH:4]=1)([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 7456MethylparabenHCID 11430Potassium Carbonate2 回HCID 45925946Tert-butyl 2-(3-cyano-4-fluorophenyl)acetate

生成物 1

HCID 68466372Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate収率 79%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
90 °C

実験手順

A flask was charged with tert-butyl 2-(3-cyano-4-fluorophenyl)acetate (9.410 g, 40.00 mmol), methyl 4-hydroxybenzoate (7.303 g, 48.00 mmol), K2CO3 (6.634 g, 48.00 mmol), and DMSO (160 mL). The mixture was heated to 90° C. under a nitrogen atmosphere for 17 hours. The mixture was cooled to ambient temperature and poured into a mixture of EtOAc (250 mL) and 10% K2CO3 solution (250 mL). The resulting insoluble residue was dissolved in water and added to the EtOAc-aqueous mixture. The mixture was stirred for 1 hour and layers were separated. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with saturated K2CO3, water, and brine, dried over MgSO4, filtered through a Celite pad, and concentrated under reduced pressure to give 14.7 g of crude product as an oil. The crude material was purified by silica gel chromatography to provide methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (11.6 g, 79%) as a white solid.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customlayers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined extracts were washed with saturated K2CO3, water, and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered through a Celite pad
  7. concentrationconcentrated under reduced pressure
  8. customto give 14.7 g of crude product as an oil
  9. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-8d94f2da184d44fc9f6ddd1d6101a908
出典データセット
uspto-grants-2013_07
特許番号
US08492437B2

反応ノート

読み込み中…