2-(2-Cyclobutylideneethyl)-3,5,6-trimethylbenzo-1,4-quinone → 5,7,8-Trimethylspiro[chromene-2,1'-cyclobutan]-6-ol

HRID 2103012Notes

Reaction equation

HRID 2103012 reaction equation
[C:1]1(=[CH:5][CH2:6][C:7]2[C:8]([C:10]([CH3:17])=[C:11]([CH3:16])[C:12](=[O:15])[C:13]=2[CH3:14])=[O:9])[CH2:4][CH2:3][CH2:2]1>N1C=CC=CC=1>[CH3:14][C:13]1[C:12]([OH:15])=[C:11]([CH3:16])[C:10]([CH3:17])=[C:8]2[C:7]=1[CH:6]=[CH:5][C:1]1([O:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 690533142-(2-Cyclobutylideneethyl)-3,5,6-trimethylbenzo-1,4-quinone

Product 1

HCID 690541785,7,8-Trimethylspiro[chromene-2,1'-cyclobutan]-6-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The above 2-(2-cyclobutylideneethyl)-3,5,6-trimethylbenzo-1,4-quinone was dissolved in pyridine and the mixture was heated to reflux for 15 h. The solvent was removed under reduced pressure and the residue was chromatographed to afford 5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-6-ol (420 mg). 1H-NMR (300. MHz, CDCl3) δ=6.59 (d, J=9.9 Hz, 1H), 6.07 (d, J=9.9 Hz, 1H), 4.39 (s, 1H), 2.47 (m, 2H), 2.26-2.17 (m, 11H), 1.90 (m, 1H), 1.75 (m, 1H) ppm. 13C-NMR (75 MHz, CDCl3) δ=145.6, 144.6, 128.9, 123.0, 122.3, 120.2, 118.5, 116.2, 37.0, 12.5, 12.3, 11.8, 11.0 ppm. MS m/z: 231 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 15 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-6073ab39581a45f39bcc29ae42c95a8e
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…