m-Chloroperbenzoic acid → HCID 10263544, compound

HRID 884461Notes

Reaction equation

HRID 884461 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].C[Si](C)(C)[O:14][C:15]1[CH:16]=[C:17]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:18]=[CH:19][C:20]=1[C:21]([O:23][Si](C)(C)C)=[CH2:22]>CO>[OH:6][CH2:23][C:21]([C:20]1[CH:19]=[CH:18][C:17]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:16][C:15]=1[OH:14])=[O:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69296470HCID 69296470, compound

Product 1

HCID 10263544HCID 10263544, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

3-Chloroperoxybenzoic acid (1.48 g, 6.0 mmol) was slurried in hexanes (40 mL) and cooled to −78° C. A solution of 4-(3-trimethylsilanyloxy-4-(1-trimethylsilanyloxy-vinyl)-phenyl]-morpholine (1.10 g, 3.01 mmol) dissolved in hexanes (5 mL) was added slowly. The resulting suspension was maintained at −78° C. for 60 minutes then slowly warmed to 22° C. After stirring at 22° C. for 16 hours, the reaction mixture was diluted with methanol and concentrated in vacuo. The residue was redissolved in methanol and concentrated two additional times. The solids were resuspended in EtOAc and washed 2 times with saturated NaHCO3, and once with saturated NaCl then dried over Na2SO4. After concentration, the residue was chromatographed on SiO2 using 2:1 hexane/EtOAc then 1:1 hexane/EtOAc. After concentration, the alcohol was recrystallized from EtOAc. (19% yield).

Workup

  1. additionwas added slowly
  2. temperatureThe resulting suspension was maintained at −78° C. for 60 minutes
  3. temperaturethen slowly warmed to 22° C
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was redissolved in methanol
  6. concentrationconcentrated two additional times
  7. washwashed 2 times with saturated NaHCO3
  8. dry with materialonce with saturated NaCl then dried over Na2SO4
  9. concentrationAfter concentration
  10. customthe residue was chromatographed on SiO2 using 2:1 hexane/EtOAc
  11. concentrationAfter concentration
  12. customthe alcohol was recrystallized from EtOAc

Sources & evidence

ORD record
ord-1671333370df45fba986d4c7eaccc45e
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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