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

HRID 885511ノート

反応式

HRID 885511 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-ac8070f6620045d08ced0ce0e8c70969
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

反応ノート

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