Ethyl vinyl ether → 8-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

HRID 27651

반응식

HRID 27651 반응식
[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([OH:14])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2].[CH2:16]([O:18][CH:19]=[CH2:20])[CH3:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CCOCC>[C:1]([O:4][CH2:5][CH2:6][CH:7]([CH3:15])[CH:8]([O:14][CH:16]([O:18][CH2:19][CH3:20])[CH3:17])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 233414518-Acetoxy-2,6-dimethyl-5-hydroxy-2-octene

생성물 1

HCID 233414488-Acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A mixture of 8-acetoxy-2,6-dimethyl-5-hydroxy-2-octene (2.27 g, 10.6 mmole), ethyl vinylether (0.82 g. 11.4 mmole), p-toluenesulfonic acid monohydrate (catalytic amount) and ether (50 ml) is stirred at room temperature for 16 hours. The resulting mixture is treated with ether (150 ml) and washes with 5% sodium bicarbonate solution (2×100 ml). The organic phase is dried (Na2SO4), and evaporated in vacuo to give the crude product. The crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane) to give 8-acetoxy-2,6-dimethyl-5-[(1-ethoxyethoxy)]-2-octene as a colorless oil.

후처리

  1. dry with materialThe organic phase is dried (Na2SO4)
  2. customevaporated in vacuo
  3. customto give the crude product
  4. customThe crude material is further purified by column chromatography on silica gel (25 g, 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-49094542a80f4e6a902dcd31a870d2f8
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04222937

연결된 노트

불러오는 중…