3,4-dihydro-2H-pyran → 2-(4-Bromo-3-methylbutoxy)oxane
Reaction equation
[Br:1][CH2:2][CH:3]([CH3:7])[CH2:4][CH2:5][OH:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>C(Cl)Cl>[Br:1][CH2:2][CH:3]([CH3:7])[CH2:4][CH2:5][O:6][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
16.7 g of 4-bromo-3-methylbutanol was dissolved in 200 ml of anhydrous methylene chloride, and with ice cooling, 10.0 g of dihydropyran was added dropwise. After the addition, the mixture was stirred at room temperature for 2 hours, and then the solvent was distilled off. The residue was purified by silica gel column chromatography using hexane/ethyl acetate as an eluent to give 16.2 g of 2-[4-bromo-3-methylbutoxy]-tetrahydro-2H-pyran. The NMR spectrum of this product was as follows:
Workup
- additionAfter the addition
- distillationthe solvent was distilled off
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-9cf4cada1a3b4855a958329b0f0ee7ff
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05077046
Reaction notes
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