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

HRID 2102982노트

반응식

HRID 2102982 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-8432fab18a064b89bf58f106b343089a
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576094B2

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