Potassium Hydroxide → 2-(4-(4-Chlorophenyl)tetrahydro-2H-pyran-4-yl)acetic acid

HRID 1375088ノート

反応式

HRID 1375088 の反応式
C([O:3][C:4](=[O:21])[CH:5]([C:8]1([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)C#N)C.[OH-].[K+]>C(O)CO.O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([CH2:5][C:4]([OH:21])=[O:3])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[CH:15][CH:16]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 69418108Ethyl 4-(4-chlorophenyl)-α-cyanotetrahydro-2H-pyran-4-acetate

生成物 1

HCID 210779472-(4-(4-Chlorophenyl)tetrahydro-2H-pyran-4-yl)acetic acid収率 125.2%

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒

実験手順

A stirred solution of (4-{4-chloro-phenyl}-tetrahydro-pyran-4-yl)-cyano-acetic acid ethyl ester (3.3 g, Reference Example 22) in ethylene glycol (50 mL) was treated with a solution of potassium hydroxide (5 g) in water (10 mL) in one portion and then heated at reflux temperature for 23 hours. The resultant pale amber solution was evaporated and the oily residue was treated with water (50 mL). The mixture was washed with diethyl ether (20 mL), then ice-cooled, then acidified to pH 1 by addition of concentrated hydrochloric acid (3 mL) and then extracted with diethyl ether (50 mL). The organic extract was washed with water (25 mL) then dried over magnesium sulfate and then evaporated to give the title compound (3.42 g) as a colourless oil, which slowly crystallised on standing. LC-MS: RT=2.92 minutes, MS(ES+): 253 and 255(M+H)+.

後処理

  1. temperatureheated
  2. temperatureat reflux temperature for 23 hours
  3. customThe resultant pale amber solution was evaporated
  4. additionthe oily residue was treated with water (50 mL)
  5. washThe mixture was washed with diethyl ether (20 mL)
  6. temperatureice-cooled
  7. additionacidified to pH 1 by addition of concentrated hydrochloric acid (3 mL)
  8. extractionextracted with diethyl ether (50 mL)
  9. extractionThe organic extract
  10. washwas washed with water (25 mL)
  11. dry with materialthen dried over magnesium sulfate
  12. customevaporated

出典と根拠

ORDレコード
ord-aea4233aeeba4efaad5aaf33e9d6b4ed
出典データセット
uspto-grants-2007_01
特許番号
US07166616B2

反応ノート

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