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

HRID 1375088노트

반응식

HRID 1375088 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-aea4233aeeba4efaad5aaf33e9d6b4ed
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166616B2

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