Aluminium lithium hydride → HCID 69907539, compound

HRID 1582681Notes

Reaction equation

HRID 1582681 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:26])=[CH:20][C:21](OCC)=[O:22])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[CH:7]1([C:13]2[CH:14]=[CH:15][C:16]([C:19]([CH3:26])=[CH:20][CH2:21][OH:22])=[CH:17][CH:18]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69907597HCID 69907597, compound

Product 1

HCID 69907539HCID 69907539, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled slurry of LiAlH4 (3.8 g) in dry ether (200 ml) was added a solution of ethyl 3-(4′-cyclohexylphenyl)-but-2-enoate (3b, 12.7 g) in dry ether (50 ml) dropwise. The reaction mixture was stirred for 3 h at 0° C. The reaction mixture was quenched with water (20 ml). A solution of 10% NaOH (10 ml) was added and the ether layer was decanted. The precipitate was washed with ether and combined extracts were concentrated. The crude product was purified by column chromatography on silica gel as adsorbent and hexane/ethylacetate as eluant to furnish 9.5 g (88.7% yield) of 3-(4′-cyclohexylphenyl)-2-butenol (4b) m.p. 54-55° C.

Workup

  1. customThe reaction mixture was quenched with water (20 ml)
  2. additionA solution of 10% NaOH (10 ml) was added
  3. customthe ether layer was decanted
  4. washThe precipitate was washed with ether
  5. concentrationwere concentrated
  6. customThe crude product was purified by column chromatography on silica gel as adsorbent and hexane/ethylacetate as eluant

Sources & evidence

ORD record
ord-ebdd63c15e034c778b7cac10f1e5afeb
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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