Diisobutylamine → 2-Chloro-4-(oxan-4-yl)phenol
Reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(NCC(C)C)C(C)C.S(Cl)([Cl:26])(=O)=O>C1(C)C=CC=CC=1>[Cl:26][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][C:10]=1[OH:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a 30 ml Toluene solution of 4-(4-tetrahydropyranyl)phenol 1 g (5.61 mmol) and diisobutylamine 0.08 ml (0.46 mmol) was added sulfuryl chloride 0.51 ml (6.35 mmol) over 3 hr period upon heating at 70° C. Stirring was continued at that temp. for 2 hr after the addition of sulfuryl chloride was complete. The solvent was removed under reduced pressure, diluted with ethyl acetate and washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes: ethyl acetate) to give 0.941 g of the title compound as while solid.
Workup
- customThe solvent was removed under reduced pressure
- additiondiluted with ethyl acetate
- washwashed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel (hexanes: ethyl acetate)
Sources & evidence
- ORD record
- ord-76698d8fdca94847baf91ee1b2cf2f62
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06465497B2
Reaction notes
Loading…