epsilon-CAPROLACTONE → 6-(4-Fluoro-3-methylbenzyloxy)hexanoic acid

HRID 885511노트

반응식

HRID 885511 반응식
[O:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:8].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][C:11]=1[CH3:18].[OH-:19].[K+]>C1(C)C=CC=CC=1.O>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:1][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:8])=[O:19])=[CH:12][C:11]=1[CH3:18]

참가 물질

6

반응물 3

HCID 10401epsilon-CAPROLACTONEHCID 14797Potassium HydroxideHCID 27781354-(Bromomethyl)-1-fluoro-2-methylbenzene

생성물 1

HCID 595125786-(4-Fluoro-3-methylbenzyloxy)hexanoic acid수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a solution of oxepan-2-one (0.562 g, 4.925 mmol) and 4-fluoro-3-methylbenzyl bromide (3.000 g, 14.774 mmol) in 20 mL of toluene, was added KOH (1.382 g, 24.625 mmol). The mixture was refluxed for 86 h. After cooling to room temperature, the reaction mixture was diluted with water (80 mL) and washed with ether. The aqueous layer was acidified with concentrated HCl to pH=2 and extracted with ether (50 mL×3). The combined organic extracts dried (Na2SO4), filtered, and concentrated under reduced pressure to give the title compound as colorless oil which was used directly in the next step without further purification (1.173 g, 94% yield). LC-MS: tR=8.0 min, m/z 277 (M+H)+.

후처리

  1. temperatureThe mixture was refluxed for 86 h
  2. washwashed with ether
  3. extractionextracted with ether (50 mL×3)
  4. dry with materialThe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ac8070f6620045d08ced0ce0e8c70969
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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