3,4-dihydro-2H-pyran → 2-(4-Bromo-3-methylbutoxy)oxane

HRID 477282Notes

Reaction equation

HRID 477282 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]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 14680533HCID 14680533, compound

Product 1

HCID 139373682-(4-Bromo-3-methylbutoxy)oxaneYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. additionAfter the addition
  2. distillationthe solvent was distilled off
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9735ef85225047049438370d31166430
Source dataset
uspto-grants-1989_12
Patent number
US04886904

Reaction notes

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