3,4-dihydro-2H-pyran → HCID 19019069, compound

HRID 1110094Notes

Reaction equation

HRID 1110094 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[CH2:6].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>Cl.C(OCC)C>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]1[O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 1513983,4-Dihydroxystyrene

Product 1

HCID 19019069HCID 19019069, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

To 100 g (0.73 mol) of the 3,4-dihydroxystyrene prepared in a) are added 320 g (3.8 mol) of dihydropyran and a few drops of concentated hydrochloric acid. The reaction mixture is stirred for 12 h at 40° C. The solution is then diluted with diethyl ether and poured on to ice. The organic phase is washed twice at 0° C. with 1N NaOH, dried, and treated with activated carbon. After filtration and concentration of the filtrate there is obtained a colourless viscous liquid which is chromatographed over a column of silica gel with a 4:1 mixture of hexane/ethyl acetate.

Workup

  1. additionpoured on to ice
  2. washThe organic phase is washed twice at 0° C. with 1N NaOH
  3. customdried
  4. additiontreated with activated carbon
  5. filtrationAfter filtration and concentration of the filtrate there
  6. customis obtained a colourless viscous liquid which
  7. customis chromatographed over a column of silica gel with a 4:1 mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-b53979eda20b49d8b2c8e99d9dbabbca
Source dataset
uspto-grants-1994_06
Patent number
US05324804

Reaction notes

Loading…