Hexamethylphosphoramide → cis-5-(11-Tetradecenyloxy)furancarboxylic acid

HRID 1111411

반응식

HRID 1111411 반응식
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14].[OH-].[Na+].Cl[C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.CN(C)P(=O)(N(C)C)N(C)C>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:1]([O:15][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14]

참가 물질

7

반응물 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 2348535-Chlorofuran-2-carboxylic acidHCID 1712010Cis-11-tetradecenol

생성물 1

HCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

8.8 g (0.0414 mole) of cis-11-tetradecen-1-ol was combined with 4.0 g (0.0829 mole) of sodium hydroxide (50% in oil) in 200 ml of dry toluene and heated to reflux with stirring for 3 hours. 6.1 g (0.414 mole) of 5-chloro-2furoic acid was added, followed by 25 ml of hexamethylphosphoric triamide (HMPA), and the reaction mixture refluxed with stirring for 20 hours, cooled, and acidified with acetic acid. The mixture was extracted into ether and the organic layer washed with water and with brine and evaporated to yield cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid, M.P. 89°-90° C.

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturethe reaction mixture refluxed
  4. stirringwith stirring for 20 hours
  5. temperaturecooled
  6. extractionThe mixture was extracted into ether
  7. washthe organic layer washed with water and with brine
  8. customevaporated

출처 및 근거

ORD 기록
ord-2fde1a579fce4f309cd39843c06b6e6b
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980371

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