Methanol → HCID 18782666, compound

HRID 1420810Notes

Reaction equation

HRID 1420810 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH2:13][CH:14]=C)[C:3]=1[OH:16].C[OH:18]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH2:13][CH2:14][OH:18])[C:3]=1[OH:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 18782489HCID 18782489, compound

Product 1

HCID 18782666HCID 18782666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Through a cooled (-78° C.) solution of 2-bromo-6-(prop-2-enyl)-4-trifluormethoxyphenol (Description 15.; 5.9 g, 0.02 mol) in dichloromethane (30 ml) and methanol (30 ml) was bubbled a mixture of ozone in oxygen for 4 h. After the solution had been purged with nitrogen for 1 h., sodium borohydride (0.755 g) was added and then stirred at room temperature for 15 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water containing (2M HCl (20 ml). The organic phase was washed with saturated brine, dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed on silica gel (eluting with 20% ethyl acetate in hexane) to give the title compound. 1H NMR (250 MHz, CDCl3) δ2.93 (2H, t, J 5.6 Hz), 3.98 (2H, t, J 5.4 Hz), 6.96 (1H, d, J 2.5 Hz), and 7.3 (1H, d, J 2.4 Hz).

Workup

  1. customwas bubbled
  2. additiona mixture of ozone in oxygen for 4 h
  3. customAfter the solution had been purged with nitrogen for 1 h.
  4. additionsodium borohydride (0.755 g) was added
  5. customThe solvent was removed in vacuo
  6. customthe residue partitioned between ethyl acetate and water containing (2M HCl (20 ml)
  7. washThe organic phase was washed with saturated brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated in vacuo
  10. customThe residue was chromatographed on silica gel (eluting with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5628337531a04dbd8359638fdb517ac6
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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