2,6-Dimethylhydroquinone → 5,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

HRID 2102982ノート

反応式

HRID 2102982 の反応式
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4].[CH:11]([C:13]1(O)[CH2:16][CH2:15][CH2:14]1)=[CH2:12]>O1CCOCC1.C(OCC)(=O)C>[CH3:10][C:5]1[C:3]([OH:4])=[C:2]([CH3:1])[CH:8]=[C:7]2[C:6]=1[CH2:12][CH2:11][C:13]1([O:9]2)[CH2:16][CH2:15][CH2:14]1

参加物

5

反応物 2

HCID 695602,6-DimethylhydroquinoneHCID 122509441-Ethenylcyclobutan-1-ol

生成物 1

HCID 115502985,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol収率 38.7%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution of 2,6-dimethylhydroquinone (2.36 g) and BF3-ether (4.47 mL) in dioxane (10 mL) was added 1-vinyl-cyclobutanol (1.58 g) in dioxane (5 mL) over 50 min at 110° C. under nitrogen. The reaction was refluxed for one additional hour. The solution was diluted with ethyl acetate and washed with water and brine, dried and evaporated. The residue was chromatographed (silica gel, hexane-ethyl acetate 1% to 5%) gave 1.36 g of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol.

後処理

  1. temperatureThe reaction was refluxed for one additional hour
  2. washwashed with water and brine
  3. customdried
  4. customevaporated
  5. customThe residue was chromatographed (silica gel, hexane-ethyl acetate 1% to 5%)

出典と根拠

ORDレコード
ord-8432fab18a064b89bf58f106b343089a
出典データセット
uspto-grants-2009_08
特許番号
US07576094B2

反応ノート

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