Acetone → Ethyl(6-(1,2-dihydroxyethyl)-1-benzothiophen-3-yl)acetate

HRID 591518Notes

Reaction equation

HRID 591518 reaction equation
O.C[N+]1([O-])CC[O:6]CC1.[CH2:10]([O:12][C:13](=[O:26])[CH2:14][C:15]1[C:19]2[CH:20]=[CH:21]C(C=C)=[CH:23][C:18]=2[S:17][CH:16]=1)[CH3:11].[CH3:27][C:28]([CH3:30])=[O:29].CC#N>[Os](=O)(=O)(=O)=O.O>[CH2:10]([O:12][C:13](=[O:26])[CH2:14][C:15]1[C:19]2[CH:20]=[CH:21][C:27]([CH:28]([OH:29])[CH2:30][OH:6])=[CH:23][C:18]=2[S:17][CH:16]=1)[CH3:11]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6342AcetonitrileHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 131734526Ethyl(6-vinyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734527Ethyl(6-(1,2-dihydroxyethyl)-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a mixture of 4-methylmorpholine 4-oxide hydrate (527 mg), ethyl(6-vinyl-1-benzothiophen-3-yl)acetate (320 mg), acetone (0.5 mL), CH3CN (0.500 mL) and water (0.500 mL) was added osmium(VIII) oxide (7% microcapsule, 472 mg) at room temperature. The mixture was stirred at room temperature for 4 d. The insoluble material was removed by filtration through Celite®, and the filtrate was concentrated in vacuo. Water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (200 mg).

Workup

  1. customThe insoluble material was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater was added to the mixture
  4. extractionthe mixture was extracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-92cb2e89c6974a909d60998011f0a214
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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