Tetrahydrofuran → HCID 10543726, compound

HRID 368372Notes

Reaction equation

HRID 368372 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][CH2:14][CH3:15].[CH2:16]1[CH2:20][O:19][CH2:18][CH2:17]1>>[CH2:2]([C:18]1[O:19][CH:20]=[CH:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 8208Myristyl bromide

Product 1

HCID 10543726HCID 10543726, compoundYield 90%

Procedure

1-Bromotetradecane (3.0 g, 9.01 mmol) in THF (4 mL) was added dropwise and the resulting solution was warmed to room temperature and stirred overnight. The reaction was quenched with a saturated solution of NH4Cl (5 mL). The organic layer was removed and the aqueous layer extracted with ether (3×5 mL). The combined organic layers were washed with a saturated solution of NaHCO3 (1×5 mL), brine (1×5 mL), dried over MgSO4, filtered and concentrated. The crude residue was passed through a small silica gel plug and recrystallized in methanol to afford the 2-(octadecyl)furan compound (22) (2.61 g, 90% yield).

Workup

  1. customThe reaction was quenched with a saturated solution of NH4Cl (5 mL)
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted with ether (3×5 mL)
  4. washThe combined organic layers were washed with a saturated solution of NaHCO3 (1×5 mL), brine (1×5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customrecrystallized in methanol

Sources & evidence

ORD record
ord-41059ab8b6d7452bb582e1d5ff3bb64a
Source dataset
uspto-grants-2000_10
Patent number
US06133313

Reaction notes

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