HCID 13309734, compound → HCID 12867349, compound

HRID 1981829Notes

Reaction equation

HRID 1981829 reaction equation
C([O:5][C:6]([C:8]1([CH3:15])[CH2:13][CH2:12][CH:11]=[C:10]([CH3:14])[O:9]1)=O)CCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:15][C:8]1([CH2:6][OH:5])[CH2:13][CH2:12][CH:11]=[C:10]([CH3:14])[O:9]1

Participants

4

Reactant 2

HCID 13309734HCID 13309734, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12867349HCID 12867349, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,4-dihydro-2,6-dimethyl-2H-pyran-2-carboxylic acid butyl ester (23.7 g) and lithium aluminum hydride (4.2 g) in 160 ml tetrahydrofuran was heated briefly to reflux and then allowed to cool. After 3.5 hours, excess hydride was destroyed by addition of ethyl acetate (70 ml). Volatile solvents were then stripped, and the residue was treated with 100 ml 15% aqueous sodium hydroxide and extracted with ether. The organic phase was dried over potassium carbonate and distilled to afford 12.3 g colorless product with bp 48°-49° C. (0.03 torr).

Workup

  1. temperaturewas heated briefly
  2. temperatureto reflux
  3. temperatureto cool
  4. customexcess hydride was destroyed by addition of ethyl acetate (70 ml)
  5. additionthe residue was treated with 100 ml 15% aqueous sodium hydroxide
  6. extractionextracted with ether
  7. dry with materialThe organic phase was dried over potassium carbonate
  8. distillationdistilled

Sources & evidence

ORD record
ord-edb4728b65c544ef8e2371a0ba0116bd
Source dataset
uspto-grants-1986_06
Patent number
US04594094

Reaction notes

Loading…