Water → 6-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

HRID 2103041Notes

Reaction equation

HRID 2103041 reaction equation
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[CH3:17][O:18]C(Cl)Cl.O>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[OH:15][C:14]1[C:2]([CH3:1])=[C:3]2[C:11](=[C:12]([CH:17]=[O:18])[C:13]=1[CH3:16])[O:10][C:6]1([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 115502985,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

Product 1

HCID 866054876-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (1 g) in DCM (20 mL) was added TiCl4 (0.53 mL) which turned the solution a red color. To the solution was added dichloromethyl methyl ether (0.42 mL) and stirred at 0° C. for 30 min and then at room temperature for 30 min. The solution was poured into water and the DCM was separated, dried and evaporated. The residue was purified by silica gel column eluting with 20% ethylacetate in hexane to give 700 mg of 6-hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-8-carbaldehyde as a yellow solid.

Workup

  1. waitat room temperature for 30 min
  2. customthe DCM was separated
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 20% ethylacetate in hexane

Sources & evidence

ORD record
ord-067d23ddd9454e42b893dfa94e086972
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…