Water → HCID 18001102, compound

HRID 478346Notes

Reaction equation

HRID 478346 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[C:4]([CH3:15])[CH:3]=1.C([Li])CCC.[C:21]1(=[O:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.O>O1CCCC1.CCCCCC>[OH:27][C:21]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=3)=[C:4]([CH3:15])[CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 18001015HCID 18001015, compoundHCID 178418339Butyllithium

Product 1

HCID 18001102HCID 18001102, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2-(4-bromo-2-methylphenyl)-4,4-dimethyl-2-oxazoline (5 g) in dry tetrahydrofuran (40 ml) is added dropwise a 1.6M solution of n-butyl lithium in n-hexane (14.0 ml) at −70° C. The mixture is stirred at the same temperature for 30 minutes, and thereto is added dropwise cyclohexanone (2.1 ml), and the mixture is stirred for one hour. To the mixture is added water, and the mixture is evaporated to remove the tetrahydrofuran, and then extracted with diethyl ether. The diethyl ether layer is dried over anhydrous magnesium sulfate, evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→60:1), recrystallized from acetone/n-hexane to give 2-[4-(1-hydroxy-1-cyclohexyl)-2-methylphenyl]-4,4-dimethyl-2-oxazoline (4.29 g) as white powder.

Workup

  1. stirringthe mixture is stirred for one hour
  2. customthe mixture is evaporated
  3. customto remove the tetrahydrofuran
  4. extractionextracted with diethyl ether
  5. dry with materialThe diethyl ether layer is dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent
  8. customthe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=100:1→60:1)
  9. customrecrystallized from acetone/n-hexane

Sources & evidence

ORD record
ord-5475e3b6fbcb4d2194ff702d72a93f74
Source dataset
uspto-grants-2003_11
Patent number
US06642223B2

Reaction notes

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