Aluminium lithium hydride → (S)-7-Benzyloxymethoxy-2,6-dimethyl-heptan-2-ol

HRID 493063Notes

Reaction equation

HRID 493063 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:20])[CH2:13][CH2:14][CH:15]1[O:18][C:16]1([CH3:19])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:20])[CH2:13][CH2:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57680482(2S)-l-Benzyloxymethoxy-2,6-dimethyl-5,6-epoxy-heptane

Product 1

HCID 57680493(S)-7-Benzyloxymethoxy-2,6-dimethyl-heptan-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the epoxide 6 (2.5 g, 9 mmol) in anhydrous ether (75 mL) at 0° C. was added lithium aluminum hydride (1.7 g, 67.5 mmol). The cooling bath was removed and the reaction was stirred at room temperature overnight. The reaction was then quenched with cold water and aqueous NH4Cl, and extracted with CH2Cl2. The solvents were removed under reduced pressure and the crude oil was chromatographed on a silica gel using hexane/EtOAc (9:1) as an eluent to give an oily alcohol 7 (2 g, 80%).

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was then quenched with cold water and aqueous NH4Cl
  3. extractionextracted with CH2Cl2
  4. customThe solvents were removed under reduced pressure
  5. customthe crude oil was chromatographed on a silica gel

Sources & evidence

ORD record
ord-a290c76dca7e4925ab92468e3f6b8029
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

Loading…