Ozone → HCID 66644089, compound

HRID 2173302Notes

Reaction equation

HRID 2173302 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH:13]=C.[O:15]=[O+][O-].[BH4-].[Na+]>CO.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[CH2:12][CH2:13][OH:15]

Participants

6

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 67517958HCID 67517958, compound

Product 1

HCID 66644089HCID 66644089, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-4-prop-2-en-1-yl-2-benzofuran-1(3H)-one (1.27 g, 5.02 mmol) in MeOH (50 mL) and DCM (50 mL) was bubbled O3 at −78° C. until the solution turned blue; excess ozone was removed on high vacuum. After the solution's color changed into colorless, NaBH4 (0.8 g, 20 mmol) was added to the reaction mixture and subsequently stirred at room temperature for 30 min; LC and TLC indicated that reaction had gone to completion; solvent was removed on high vacuum, the residue was then re-dissolved in EtOAc and washed with water, dried over Na2SO4, filtered and concentrated to dryness. The organic residue was absorbed into silica gel and was separated on silica gel column to give 5-bromo-4-(2-hydroxyethyl)-2-benzofuran-1(3H)-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.7 (d, J=7.8 Hz, 1H), 7.5 (d, J=7.8 Hz, 1H), 5.37 (s, 2H), 3.94 (t, J=6.3 Hz, 2H), 2.98 (t, J=6.3 Hz, 2H)

Workup

  1. customexcess ozone was removed on high vacuum
  2. additionwas added to the reaction mixture
  3. customLC and TLC indicated that reaction
  4. customsolvent was removed on high vacuum
  5. dissolutionthe residue was then re-dissolved in EtOAc
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe organic residue was absorbed into silica gel
  11. customwas separated on silica gel column

Sources & evidence

ORD record
ord-82a361a34e594f0d8e627521495b2289
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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