2H-Pyran, 2-[(12-bromododecyl)oxy]tetrahydro- → 2-[(12-Cyclohexyldodecyl)oxy]oxane
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.[CH:21]1([Mg]Br)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH:21]1([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1Participants
3
Procedure
57.8 g (165 millimole) of 2-[(12-bromododecyl}oxy]tetrahydro-2H-pyran and 39.6 g (247 millimole) of cyclohexyl magnesium bromide were reacted by following a procedure similar to that of Working Example 16, to give crude 2-[(12-cyclohexyldodecyl)oxy]tetrahydro-2H-pyran. This crude product was dissolved in 450 ml of methanol, to which 4.5 g of Amberlist® H-15 was added, and the resulting mixture was stirred at 45° C. for 2 hours. The resin was filtrated off, and the filtrate was concentrated to dryness under reduced pressure. The residue wa subjected to column chromatography on silica gel (1 kg), and eluted with hexane-ethyl acetate (6:1), to give the above-captioned compound as colorless solid.
Sources & evidence
- ORD record
- ord-a679067743004e34adc92c330bb429bd
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04889953
Reaction notes
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