HCID 86605482, compound → HCID 11579635, compound

HRID 2103027Notes

Reaction equation

HRID 2103027 reaction equation
CO[CH:3]1[CH2:6][CH2:5][C:4]21[CH:15]([CH3:16])[CH2:14][C:13]1[C:8](=[C:9]([CH3:20])[C:10]([CH3:19])=[C:11]([OH:18])[C:12]=1[CH3:17])[O:7]2>CO.Cl>[CH3:16][C:15]1[C:4]2([CH2:5][CH2:6][CH2:3]2)[O:7][C:8]2[C:13](=[C:12]([CH3:17])[C:11]([OH:18])=[C:10]([CH3:19])[C:9]=2[CH3:20])[CH:14]=1

Participants

4

Reactant 1

HCID 86605482HCID 86605482, compound

Product 1

HCID 11579635HCID 11579635, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methoxy-3,5,7,8-tetramethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (50 mg) in 10 mL of MeOH was added 5 drops of conc. HCl. The reaction mixture was concentrated, and the residue was purified by flash chromatography eluted with 20% ethyl acetate in hexane to give 40.5 mg of the desired product 3,5,7,8-tetramethylspiro[chromene-2,1′-cyclobutan]-6-ol as a white solid. 1H-NMR (300 MHz, CDCl3) δ=6.27 (s, 1H, =CH), 4.28 (s, 1H), 2.39 (t, 2H), 2.22 (s, 3H), 2.17 (s, 6H), 2.03 (s, 3H), 2.10-1.70 (m, 4H) ppm. 13C-NMR (75 MHz, CDCl3) δ=145.7, 143.7, 136.0, 122.3, 121.6, 119.9, 116.6, 115.1, 81.3, 33.3, 19.1, 14.2, 12.7, 11.8, 11.4 ppm. MS: (m/z)=245.1 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a6c939141b56419c9548e04eaaacbb62
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…