Ethyl formate → 2-Formylheptanonitrile

HRID 1110367

반응식

HRID 1110367 반응식
C[C:2](C)([O-:4])C.[K+].[C:7](#[N:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(OCC)=O.CC(C)([O-])C>C1(C)C=CC=CC=1.O.CCOCC.O1CCCC1>[CH:2]([CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:7]#[N:14])=[O:4]

참가 물질

9

반응물 4

HCID 8025Ethyl formateHCID 12372HeptanenitrileHCID 45749132-Methylpropan-2-olateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 198955292-Formylheptanonitrile수율 77%

시약·촉매·용매 4

HCID 962Water용매HCID 1140Toluene용매2회HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of potassium tert-butoxide (18.9 g) in a mixed solvent system of tetrahydrofuran (150 ml) and toluene (100 ml) was heated to 75°. A solution of heptanonitrile (11.2 g) and ethyl formate (24 ml) in toluene (50 ml) was then added dropwise to the warm tert-butoxide solution. The reaction was stirred for 5 hours at 75° then cooled with an ice bath. Ether was added to the mixture and then water. The layers were separated. The aqueous phase was washed once with ether then acidified to a pH of about 3 with aqueous hydrochloric acid (6N). The aqueous phase was saturated with sodium chloride then extracted twice with ether. The combined ether extracts were washed with brine, dried (MgSO4) and concentrated to leave the title product as a yellow oil (10.7 g, 77%).

후처리

  1. temperaturethen cooled with an ice bath
  2. customThe layers were separated
  3. washThe aqueous phase was washed once with ether
  4. extractionthen extracted twice with ether
  5. washThe combined ether extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d4a86103d4044a29a5de166587291c39
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975435

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