Dimethyl Sulfoxide → HCID 59565751, compound

HRID 2075959Notes

Reaction equation

HRID 2075959 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([CH:15]([OH:17])[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(C)=O.O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([C:18]2[N:22]=[C:21]([CH3:23])[O:20][N:19]=2)=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 962WaterHCID 8471TriethylamineHCID 59565653HCID 59565653, compound

Product 1

HCID 59565751HCID 59565751, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[5-benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]ethanol (reference example 6-2) (467 mg), triethylamine (0.956 mL) and dimethyl sulfoxide (6 mL) was added a mixture of pyridine sulfur trioxide complex (655 mg) and dimethyl sulfoxide (2 mL). After stirring at room temperature for 2 hours, water and ethyl acetate were added to the mixture. The separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 25%-34% ethyl acetate/hexane, gradient elution) to give the title compound (365 mg).

Workup

  1. additionwas added
  2. washThe separated organic layer was washed with 2 mol/L hydrochloric acid and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: 25%-34% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-d821afbfaed949a0a9b61af0d1450d86
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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