tert-Butanol → HCID 66841935, compound

HRID 2267698Notes

Reaction equation

HRID 2267698 reaction equation
[CH2:1]([N:8]1CC=C[CH:10]([CH3:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:19]CC1.[C:23]([OH:27])([CH3:26])(C)[CH3:24].S(=O)(O)[O-].[Na+]>O.CC(C)=O.[Os](=O)(=O)(=O)=O>[CH2:1]([N:8]1[CH2:9][CH:10]([CH3:14])[CH:24]([OH:19])[CH:23]([OH:27])[CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 20836761HCID 20836761, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 66841935HCID 66841935, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

37 (570 mg, 3 mmol) is dissolved in 10 ml of a 1:1 mixture of water and acetone. After addition of N-methyl-morpholine-N-oxide (529 mg, 4.5 mmol), a 2.5% solution of osmium tetroxide in tert. Butanol (527 ul, 52 umol) is added. The mixture is stirred at room temperature for 24 h. Then 10 ml of a saturated sodium bisulfite solution is added. After 15 min stirring at room temperature, the reaction mixture is extracted with ethyl acetate. The organic layers are washed subsequently with 1N NaOH and brine, dried over sodium sulphate and evaporated. The crude product, 460 mg of a dark brown oil, is purified by Flash-chromatography (silica gel, dichloromethane/methanol/ammonia 95:5:0.5).

Workup

  1. stirringAfter 15 min stirring at room temperature
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe organic layers are washed subsequently with 1N NaOH and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe crude product, 460 mg of a dark brown oil, is purified by Flash-chromatography (silica gel, dichloromethane/methanol/ammonia 95:5:0.5)

Sources & evidence

ORD record
ord-0e394b91d3f6438ba0e911df6875c537
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

Loading…