Water → 1-Methoxy-7-(4-pentenyloxy)heptane

HRID 1600420Notes

Reaction equation

HRID 1600420 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].Br[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].O>O1CCCC1>[CH3:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 154095297-Methoxy-1-heptanol

Product 1

HCID 154095301-Methoxy-7-(4-pentenyloxy)heptaneYield 16.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (665 mg, 17 mmol, washed three times with hexane) was treated with the title product of Example 3 (2.0 g, 14 mmol) in 90 mL of tetrahydrofuran at ref lux for one hour. A solution of 5-bromopentene (2.0g, 14 mmol) in 50 mL of tetrahydrofuran was added dropwise and refluxing continued for 20 hours. After cooling to room temperature, 50 mL of water was added, the layers separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Chromatography of the crude residue on silica gel using 50-50 ethyl acetate-heptane as eluant gave the title compound (485 mg) as a yellow oiland the structure verified by NMR.

Workup

  1. temperaturerefluxing
  2. customthe layers separated
  3. extractionthe aqueous phase was extracted with two portions of ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5216c18f24c54ddea3669903ae5d461d
Source dataset
uspto-grants-1998_04
Patent number
US05744631

Reaction notes

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