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

HRID 2262366ノート

反応式

HRID 2262366 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5881176(Z)-1,1,1,2,2,3,3-Heptafluoro-6-hydroxy-7,7-dimethyloct-5-en-4-one;ytterbium触媒HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e73cbe7b45943638b360b110e5f8b9c
出典データセット
uspto-grants-2010_12
特許番号
US07851072B2

反応ノート

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