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

HRID 649226

반응식

HRID 649226 반응식
[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]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acidHCID 178418348HCID 178418348, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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. 3638° C.

후처리

  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

출처 및 근거

ORD 기록
ord-868fae1ecd7740ab9c5c90e051fa1a9d
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04738984

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