Methyl morpholine oxide → 5-(1,2-Dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

HRID 1848414Notes

Reaction equation

HRID 1848414 reaction equation
[CH3:1][C:2]1[C:10](/[CH:11]=[CH:12]/[CH3:13])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:14].C[N+]1([O-])CC[O:19]CC1.C(#N)C.[OH2:26]>O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[OH:26][CH:11]([C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:14])[O:5][CH2:4]2)[CH:12]([OH:19])[CH3:13]

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18373917Acetonitrile--water (1/1)HCID 86709439(E)-4-Methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one

Product 1

HCID 867094405-(1,2-Dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 53393272Potassium osmate(VI) dihydrateCatalyst

Procedure

To (E)-4-methyl-5-(prop-1-en-1-yl)isobenzofuran-1(3H)-one (300 mg, 1.59 mmol) in acetonitrile/water (10/1, 18 mL) was added NMO (243 mg, 2.07 mmol) and potassium osmate(VI) dihydrate (29.4 mg, 0.080 mmol) at 0° C. The reaction mixture was allowed to warm to rt and stirred at rt for 2 h. TLC showed the reaction completed. The reaction mixture was filtered through a pad of silica gel, rinsed with 10% MeOH/DCM. The crude product was purified with column chromatography (0-10% MeOH/DCM) to give the title compound. LC/MS: [(M+1)]+=223

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washrinsed with 10% MeOH/DCM
  3. customThe crude product was purified with column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-332d0225e33146ba9da581de9bc31f7e
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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