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

HRID 2102981Notes

Reaction equation

HRID 2102981 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-90b16db4ea2e4f2ba78bf4ffc255a438
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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