Tetrahydrofuran → HCID 19917135, compound

HRID 1464772Notes

Reaction equation

HRID 1464772 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=2)[CH2:9][O:10][CH2:11][C:12]#[C:13][CH2:14][OH:15])=[CH:2]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=2)[CH2:9][O:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][OH:15])=[CH:2]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 19917052HCID 19917052, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19917135HCID 19917135, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.48 g of the resulting alcohol compound was dissolved in 5 ml of tetarahydrofuran, and under a nitrogen atmosphere, a tetrahydrofuran solution (5 ml) of 78 mg of lithium aluminum hydride was added. The mixture was stirred under ice cooling for 2 hours, and then at room temperature for 1 hour. Ethyl acetate and water were added, and the organic layer separated was worked up in a customary manner. The product was purified by silica gel column chromatography [hexane / ethyl acetate=4/1] to give 0.28 g of the captioned compound as a colorless oil.

Workup

  1. waitat room temperature for 1 hour
  2. customthe organic layer separated
  3. customThe product was purified by silica gel column chromatography [hexane / ethyl acetate=4/1]

Sources & evidence

ORD record
ord-51007e1da82b4e649e335e94d6c92a19
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

Loading…