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

HRID 649225

反応式

HRID 649225 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒

実験手順

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-2-furoic 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.

後処理

  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

出典と根拠

ORDレコード
ord-0279fa8d7ede46d0841dfd25491599dc
出典データセット
uspto-grants-1988_04
特許番号
US04738984

関連ノート

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