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1-Ethenylcyclobutan-1-ol → 5,8-Dimethyl-7-(3-methylbutyl)-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

HRID 2102981
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HRID 2102981 반응식
[CH3:1][C:2]1[C:8]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[C:7]([OH:14])[C:6]([CH3:15])=[CH:5][C:3]=1O.[CH:16]([C:18]1([OH:22])[CH2:21][CH2:20][CH2:19]1)=[CH2:17]>O1CCOCC1.C(OCC)(=O)C>[CH3:15][C:6]1[C:7]([OH:14])=[C:8]([CH2:9][CH2:10][CH:11]([CH3:12])[CH3:13])[C:2]([CH3:1])=[C:3]2[C:5]=1[CH2:17][CH2:16][C:18]1([O:22]2)[CH2:21][CH2:20][CH2:19]1
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참가 물질

5

반응물 2

HCID 122509441-Ethenylcyclobutan-1-olHCID 866054732,5-Dimethyl-3-(3-methylbutyl)hydroquinone

생성물 1

HCID 115873465,8-Dimethyl-7-(3-methylbutyl)-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol수율 45.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매2회

실험 절차

To a solution of 2,5-dimethyl-3-(3-methylbutyl)hydroquinone (208 mg) and BF3-ether (0.25 mL) in dioxane (3 mL) was added 1-vinyl-cyclobutanol (98 mg) in dioxane (3 mL) over 50 min at 110° C. degree under nitrogen. The reaction was refluxed for one additional hour. The solution was diluted with ethyl acetate and washed with water and brine, and dried. After evaporation the residue waschromatographed (silica gel, hexane-ethyl acetate 0% to 3%) gave 5,8-dimethyl-7-(3-methylbutyl)-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (130 mg).

후처리

  1. temperatureThe reaction was refluxed for one additional hour
  2. washwashed with water and brine
  3. customdried
  4. customAfter evaporation the residue

출처 및 근거

ORD 기록
ord-90b16db4ea2e4f2ba78bf4ffc255a438
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576094B2

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