Aluminium lithium hydride → HCID 69907451, compound

HRID 1582686Notes

Reaction equation

HRID 1582686 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:28])=[CH:22][C:23](OCC)=[O:24])=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>CCOCC>[CH:7]1([C:15]2[CH:16]=[CH:17][C:18]([C:21]([CH3:28])=[CH:22][CH2:23][OH:24])=[CH:19][CH:20]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69906260HCID 69906260, compound

Product 1

HCID 69907451HCID 69907451, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled slurry of LiAlH4 (2.9 g) in dry ether (200 ml) was added a solution of ethyl 3-(4′-cyclooctylphenyl)-but-2-enoate (3d, 10 g) in dry ether (50 ml) dropwise. The reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched with water (11 ml). A solution of 10% NaOH (10 ml) was added and 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 to give 6.82 g (79.3% yield) of 3-(4′-cyclooctylphenyl)-2-butenol (4d, formula 4, R=cyclooctyl) m.p. 40-44° C.

Workup

  1. customThe reaction mixture was quenched with water (11 ml)
  2. additionA solution of 10% NaOH (10 ml) was added
  3. customether 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

Sources & evidence

ORD record
ord-6a1a94bf357b45feb67fde86076f2be9
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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