Dimethyl Sulfoxide → HCID 67110067, compound

HRID 2381239Notes

Reaction equation

HRID 2381239 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:24][CH3:25])=[CH:11][C:12]([Br:23])=[C:13]([CH:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[OH: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]([Br:23])=[C:13]([C:15]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 67110285HCID 67110285, compound

Product 1

HCID 67110067HCID 67110067, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-benzyloxy-2-bromo-4-methoxyphenyl)-cyclohexylmethanol (Reference example 9-2) (580 mg), triethylamine (0.797 mL) and dimethylsulfoxide (21 mL) was added pyridine sulfur trioxide complex (684 mg) under ice-bath cooling. After stirring at room temperature for an hour, water and ethyl acetate were added to the mixture. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution) to give the title compound (348 mg).

Workup

  1. additionwas added pyridine sulfur trioxide complex (684 mg) under ice-bath
  2. temperaturecooling
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: 0%-50% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-fd0030c1021d4524ae0a848955abbe1f
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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