Diethyl Ether → HCID 19780704, compound
Reaction equation
C[Mg]I.[OH:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[CH2:13][CH2:14][CH2:15]C(O)=O.[Cl-].[NH4+].[CH2:21]1CCCCC1.CC[O:29][CH2:30][CH3:31]>>[OH:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[CH2:13][CH2:14][CH2:15][C:30]([CH3:31])([OH:29])[CH3:21]Participants
Conditions
- Temperature
- 5 °C
Procedure
A 3M ethereal solution of methylmagnesium iodide (8 ml, 24 mM) was added dropwise to a stirred solution of the lactone (C) (1.8 g, 9.5 mM) in ether (42 ml) at 5° C. Stirring was continued at ambient temperature for 12 hours. The mixture was then cooled to 5° C., treated with excess saturated ammonium chloride solution and extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and the solvent removed by evaporation. The residual oil was purified by flash chromatography, eluting with dichloromethane/ethyl acetate (9:1 v/v increasing in polarity to 8:2 v/v) to give 5-(2-hydroxy-4,6-dimethylphenyl)-2-methylpentan-2-ol (D) (1 g, 48% yield), m.p. 128° C. (after recrystallisation from cyclohexane); NMR (d6 -DMSO): 0.95(6H,s), 1.33(4H,m), 1.97(3H,s), 2.01(3H,s), 2.37(2H,s), 6.24(1H,s), 6.28(1H,s); microanalysis, found: C, 75.6; H,10.2%; C14H22O2 requires: C,75.6; H,10.0%.
Workup
- extractionextracted with ether
- washThe combined extracts were washed with brine
- dry with materialdried (Na2SO4)
- customthe solvent removed by evaporation
- customThe residual oil was purified by flash chromatography
- washeluting with dichloromethane/ethyl acetate (9:1 v/v increasing in polarity to 8:2 v/v)
- customto give
Sources & evidence
- ORD record
- ord-b4c2c95d7f9e4fb2b4ad1f8a0e35f9f5
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05185452
Reaction notes
Loading…