Aluminium lithium hydride → HCID 69475784, compound

HRID 1582689Notes

Reaction equation

HRID 1582689 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([OH:12])(=O)[CH:8]=[CH:9][CH3:10].[C:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[C:13]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:18]=[CH:17][C:16]([C:9]([CH3:10])=[CH:8][CH2:7][OH:12])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86591447HCID 86591447, compound

Product 1

HCID 69475784HCID 69475784, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled slurry of LiAlH4 (4.0 g) in dry ether (400 ml) was added ethyl 3-([1,1′-biphenyl]-but-2-enoate (3e, 11 g) in dry ether (200 ml) dropwise. The mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched with water (10 ml). A solution of 10% NaOH (5 ml) was added, stirred and then ether layer was decanted. The precipitate was washed with ether and combined ether extracts were concentrated. The crude product was purified by chromatography on silica gel to give 7.2 g (77.4% yield) of 3-([1,1′-biphenyl]-4yl)-2-butenol (4e formula 4, R=Ph), m.p. 112-114° C.

Workup

  1. customThe reaction mixture was quenched with water (10 ml)
  2. additionA solution of 10% NaOH (5 ml) was added
  3. stirringstirred
  4. customether layer was decanted
  5. washThe precipitate was washed with ether and combined ether extracts
  6. concentrationwere concentrated
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3957dfeda72b4732b1b410fb1995bb38
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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