Tetrahydrofuran → HCID 18920430, compound

HRID 1599503Notes

Reaction equation

HRID 1599503 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]=[O:10].[Cl-].[NH4+].O1CC[CH2:15][CH2:14]1>>[OH:10][CH:9]([CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[C:14]#[CH:15]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 109756032-[(Tetrahydro-2H-pyran-2-yl)oxy]acetaldehyde

Product 1

HCID 18920430HCID 18920430, compoundYield 76%

Procedure

Acetylene gas was bubbled into tetrahydrofuran (30 ml) for 30 minutes. Ethyl magnesium bromide (25 ml) was added. 2-(Tetrahydro-2-pyranyloxy)-acetaldehyde (5.0 g, 0.035 mole) in tetrahydrofuran (25 ml) was then added. The reaction mixture was warmed to room temperature and stirred overnight. Saturated ammonium chloride aqueous solution (30 ml) was added to quench the unreacted acetylide and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated and separated by silica gel chromatography eluted with n-hexane/ethyl acetate (5:2) to give colorless oil (4.5 g, 76%).

Workup

  1. customAcetylene gas was bubbled into tetrahydrofuran (30 ml) for 30 minutes
  2. additionEthyl magnesium bromide (25 ml) was added
  3. customto quench the unreacted acetylide
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customseparated by silica gel chromatography
  8. washeluted with n-hexane/ethyl acetate (5:2)

Sources & evidence

ORD record
ord-3de9c6374ce849b8a82e20e371322038
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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