Hydrochloric Acid → 2-[4-(2-Hydroxyiminocyclopentan-1-ylmethyl)phenyl]propionic Acid

HRID 971871노트

반응식

HRID 971871 반응식
[OH:1][N:2]=[C:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.C([Li])CCC.I[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[C:22]([O:24]CC)=[O:23])=[CH:17][CH:16]=1.Cl.[OH-].[Na+]>O1CCCC1.CO.O.CCCCCC>[OH:1][N:2]=[C:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([CH3:27])[C:22]([OH:24])=[O:23])=[CH:19][CH:20]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 14500Cyclopentanone, oximeHCID 14798Sodium HydroxideHCID 21312279Ethyl 2-(4-iodomethylphenyl)propionateHCID 178418339Butyllithium

생성물 1

HCID 737697752-[4-(2-Hydroxyiminocyclopentan-1-ylmethyl)phenyl]propionic Acid수율 56.8%

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a solution of 2.0 g of hydroxyiminocyclopentane in 30 ml of tetrahydrofuran was added 28 ml of 15% n-hexane solution of n-butyllithium at room temperature. After the mixture was stirred for 30 minutes at the same temperature, a solution of 6.0 g of ethyl 2-(4-iodomethylphenyl)propionate in 20 ml of tetrahydrofuran was added and stirring was continued for further 10 minutes at room temperature. The reaction mixture was poured into a mixture of 80 ml of ice-water and 20 ml of concentrated hydrochloric acid, extracted with ether, the solvent removed by distillation to afford a residue, to which 1.0 g of sodium hydroxide and 40 ml of methanol were added and the mixture was allowed to stand at room temperature overnight. To the reaction mixture was added 30 ml of water, methanol was removed by distillation, and the residual aqueous layer was shaken with ether and then acidified with hydrochloric acid. Extraction of the acidified layer with ether and decoloration of the product through a silica gel column afforded 2.8 g of the desired compound, which by recrystallization from a mixture of ether and n-hexane yielded colorless crystals, m.p. 146°-148° C.

후처리

  1. stirringstirring
  2. waitwas continued for further 10 minutes at room temperature
  3. extractionextracted with ether
  4. customthe solvent removed by distillation
  5. customto afford a residue
  6. waitto stand at room temperature overnight
  7. customwas removed by distillation
  8. stirringthe residual aqueous layer was shaken with ether
  9. extractionExtraction of the acidified layer with ether and decoloration of the product through a silica gel column

출처 및 근거

ORD 기록
ord-5917459c9a434830a74ab82551b12f53
출처 데이터셋
uspto-grants-1979_07
특허 번호
US04161538

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