Aluminium lithium hydride → 3-(4'-Chloro-[1,1'-biphenyl]-4-yl)-butenol

HRID 1582694Notes

Reaction equation

HRID 1582694 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:27])=[CH:21][C:22](OCC)=[O:23])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:27])[CH:21]=[CH:22][OH:23])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69798367Ethyl 3-(4'-chloro-[1,1'-biphenyl]-4-yl)-but-2-enoate

Product 1

HCID 699074643-(4'-Chloro-[1,1'-biphenyl]-4-yl)-butenolYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled slurry of LiAlH4 (1.4 g) in dry ether (200 ml) was added a solution of ethyl 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-but-2-enoate (3g, 2.8 g) in dry ether (50 ml) dropwise. The reaction mixture was stirred for 2 h at 0° C. The reaction mixture was quenched with water. A solution of 10% NaOH was added and the ether layer was decanted. The precipitate was washed with ether and the combined ether extract was concentrated. The crude product was chromatographed on silica gel to give 1.8 g (75% yield) of 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-butenol (4g, formula 4, R=p-Cl—C6H4) m.p. 130-132° C.

Workup

  1. customThe reaction mixture was quenched with water
  2. additionA solution of 10% NaOH was added
  3. customthe ether layer was decanted
  4. washThe precipitate was washed with ether
  5. extractionthe combined ether extract
  6. concentrationwas concentrated
  7. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-f43732996770457fae33669c25a85ec9
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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