Acetic Acid → 5-Tetradecylthio-2-furoic acid

HRID 2420268노트

반응식

HRID 2420268 반응식
Br[C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH2:10]([SH:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH2:10]([S:24][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 646771-TetradecanethiolHCID 685115-Bromo-2-furanecarboxylic acid

생성물 1

HCID 123615095-Tetradecylthio-2-furoic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C.

후처리

  1. temperatureis heated on a steam bath overnight
  2. temperaturethen refluxed for one-half hour
  3. temperatureThe mixture is then cooled
  4. extractionextracted with ether-water
  5. washThe ether layer is washed with water and salt water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate is evaporated to dryness
  9. customthe remaining solid is recrystallized from hexane and from methanol

출처 및 근거

ORD 기록
ord-32809c65a65c490d9043cf025ae10eea
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04110351

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