Ethyl 1-propenyl ether → 2-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene

HRID 2096092노트

반응식

HRID 2096092 반응식
[CH2:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[CH:13]([O:16][CH2:17][CH3:18])=[CH:14][CH3:15]>ClC(Cl)C.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.CC(C)(C)/C(/O)=C/C(C(C(C(F)(F)F)(F)F)(F)F)=O.[Yb]>[CH2:17]([O:16][CH:13]1[CH:14]([CH3:15])[CH2:1][C:2]2[CH2:11][CH2:10][C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[O:12]1)[CH3:18]

참가 물질

5

반응물 2

HCID 13570Ethyl 1-propenyl etherHCID 3777512-Methylenetetralin-1-one

생성물 1

HCID 592948342-Ethoxy-3-methyl-3,4,5,6-tetrahydrobenzo[h]chromene수율 203.2%

시약·촉매·용매 2

HCID 5881176(Z)-1,1,1,2,2,3,3-Heptafluoro-6-hydroxy-7,7-dimethyloct-5-en-4-one;ytterbium촉매HCID 63651,1-Dichloroethane용매

실험 절차

A solution of 2-methylene-3,4-dihydronaphthalen-1-one (44.9 g, 282 mmol), tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium [Yb(fod)3, 15.0 g, 14.2 mmo], and ethyl propenyl ether (300 g, 390 mL, 3.5 mol) in 830 mL of dichloroethane was heated at reflux under nitrogen with stirring for 20 hours. Evaporation of the solvent left 200 g of a brown liquid that was purified on a silica gel column with 15/85 ethylacetate/hexane as the eluent, yielding 140 g of product, which was used without further purification.

후처리

  1. temperatureat reflux under nitrogen
  2. customEvaporation of the solvent
  3. waitleft 200 g of a brown liquid that
  4. customwas purified on a silica gel column with 15/85 ethylacetate/hexane as the eluent

출처 및 근거

ORD 기록
ord-d5bde7b573ce4de2881d3cba60c508f6
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08449990B2

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