Diethyl Ether → Methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone

HRID 1111412

反応式

HRID 1111412 の反応式
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=O)=[CH:18][CH:17]=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].[CH3:24]COCC.C[Li].[Cl-].[NH4+]>C(O)(=O)C>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([CH3:24])=[O:23])=[CH:18][CH:17]=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

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acidHCID 178418348HCID 178418348、化合物

生成物 1

HCID 13655996Methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4.2 g (0.013 mole) of cis-5-(11-tetradecenyloxy) furan-2-carboxylic acid and 50 ml of anhydrous ether was stirred at room temperature and 20.2 ml (0.0313 mole) of methyllithium (1.55 molar in hexane) added over 15 minutes. The mixture was stirred at room temperature for 3 hours and poured into saturated ammonium chloride solution. About 10 ml of glacial acetic acid was added and the phases separated. The ether layer was washed with water and evaporated to dryness to give a light yellow semisolid residue which was recrystallized twice from methanol to give methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone, M.P. 36°-38° C.

後処理

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. customthe phases separated
  3. washThe ether layer was washed with water
  4. customevaporated to dryness
  5. customto give a light yellow semisolid residue which
  6. customwas recrystallized twice from methanol

出典と根拠

ORDレコード
ord-31305e23a7fd45279e6352233df5622e
出典データセット
uspto-grants-1990_12
特許番号
US04980371

関連ノート

読み込み中…