Acetone → 5-(2,3-dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

HRID 1848548Notes

Reaction equation

HRID 1848548 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1CC=C.C[N+]1([O-])CC[O:19]CC1.[CH3:23][C:24]([CH3:26])=[O:25]>O.O=[Os](=O)(=O)=O>[OH:25][CH:24]([CH2:26][OH:19])[CH2:23][C:3]1[C:2]([CH3:1])=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:11])[O:8][CH2:9]2

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 666465364-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one

Product 1

HCID 867095315-(2,3-dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 4-methyl-5-prop-2-en-1-yl-2-benzofuran-1(3H)-one (see step A for 1-3), (2.00 g, 10.6 mmol) in acetone (30 mL) and water (10 mL) was added OsO4 (0.27 g, 1.06 mmol) and NMO (6.70 g, 11.7 mmol), the solution was stirred at 25° C. for 18 h. The reaction mixture was diluted with water (30 mL) and the aqueous layer was extracted with CH2Cl2 (3×40 mL). The organic layers were combined, washed with brine (2×40 mL), dried with MgSO4, filtered and concentrated. The residue was purified by flash column chromatography (0-10% methanol in dichloromethane) to give the title compound.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×40 mL)
  2. washwashed with brine (2×40 mL)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2b742252ad134729acd022f412f865fa
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…