Boron trifluoride etherate → HCID 11048112, compound

HRID 565674Notes

Reaction equation

HRID 565674 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[C:6]([CH3:12])[C:5]([CH3:13])=[CH:4][C:3]=1[CH3:14].[CH2:15]([Li])CCC.CCCCCC.[S:26]([C:35]1[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=1)([O:29][C@H:30](C)[CH:31]1[O:33][CH2:32]1)(=[O:28])=[O:27].B(F)(F)F.CCOCC>O1CCCC1.O>[CH3:39][C:38]1[CH:40]=[CH:41][C:35]([S:26]([O:29][CH2:30][C@@:31]([OH:33])([CH3:32])[CH2:12][C:6]2[C:5]([CH3:13])=[CH:4][C:3]([CH3:14])=[C:2]([CH3:15])[C:7]=2[O:8][CH2:9][O:10][CH3:11])(=[O:28])=[O:27])=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10988982HCID 10988982, compoundHCID 86756223HCID 86756223, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 11048112HCID 11048112, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-3-(methoxymethoxy)-1,4,5-trimethylbenzene (3.0 g) in tetrahydrofuran (30 mL) was added 1.6M n-butyllithium/hexane (7.0 mL) dropwise at −78° C. and the mixture was stirred for 15 minutes. To this mixture were added (R)-methylglycidyl tosylate (2.8 g) and boron trifluoride-diethyl ether (1.5 mL), and the resulting mixture was further stirred for 15 minutes. The reaction mixture was warmed up to the room temperature, then diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=3.1) to provide (R)-2-hydroxy-3-[2-(methoxymethoxy)-3,4,6-trimethylphenyl]-2-methylpropyl 4-methylbenzene-sulfonate. This compound was dissolved in methanol (20 mL), followed by addition of potassium carbonate (1.6 g) under ice-cooling and the mixture was stirred for 30 minutes. To this reaction mixture were added ethyl acetate and water and the resulting two layers were separated. The aqueous layer was extracted with ethyl acetate and the extract was combined with the organic layer separated as above. The combined organic solution was washed with saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to provide the title compound (0.73 g). the yield based on 2-bromo-3-(methoxymethoxy)-1,4,5-trimethylbenzene=25%.

Workup

  1. stirringthe resulting mixture was further stirred for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dddc5901e2bc4375b6597888ce904dac
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

Loading…