Lithium hydride → HCID 12121236, compound

HRID 986189Notes

Reaction equation

HRID 986189 reaction equation
[C-:1]1([CH:6](CC)[C:7](O)=[O:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:17].[H-].[Li+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C-:12]1([CH:7]([OH:8])[CH2:6][CH2:1][CH3:2])[CH:16]=[CH:15][CH:14]=[CH:13]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:17]

Participants

5

Reactant 3

HCID 62714Lithium hydrideHCID 21226445Aluminium lithium hydrideHCID 129776916HCID 129776916, compound

Product 1

HCID 12121236HCID 12121236, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Acid (2) (12 g) was dissolved in ether (distilled from sodium/potassium) and treated with lithium hydride (1.27 g) in a nitrogen atmosphere. When reaction was complete the excess lithium aluminium hydride was destroyed using ethyl acetate and then water. The organic phases were separated and the aqueous phase washed with ether (2×20 ml). The organic phases were combined and dried (MgSO4) and after filtration the solvent was removed on the rotary evaporator 4. The red oil resulting had two components. Column chromatography (30 cm×2 cm) on silica eluted with 1:1 ether:hexane gave the alcohol and an ester.

Workup

  1. customWhen reaction
  2. customwas destroyed
  3. customThe organic phases were separated
  4. washthe aqueous phase washed with ether (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationafter filtration the solvent
  7. customwas removed on the rotary evaporator 4
  8. customThe red oil resulting
  9. washColumn chromatography (30 cm×2 cm) on silica eluted with 1:1 ether

Sources & evidence

ORD record
ord-85052c1b3ffa40e78fb5938dae89afea
Source dataset
uspto-grants-1987_12
Patent number
US04711245

Reaction notes

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