Methanol → HCID 11074071, compound

HRID 1856439Notes

Reaction equation

HRID 1856439 reaction equation
[CH:1]([Li])=[CH2:2].[C:4]1([CH:14]=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.CO.CCOCC>C1COCC1>[C:4]1([CH:14]([OH:15])[CH:1]=[CH2:2])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 61951-NaphthaldehydeHCID 178506890HCID 178506890, compound

Product 1

HCID 11074071HCID 11074071, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of vinyl lithium (2.04 g, 0.06 mole, 2.5 ml) in dry THF (30 ml) under N2 with stirring, at -60° was added dropwise a solution of naphthaldehyde (4.68 g, 0.03 mole) in 10 ml THF. The reaction was kept at -60° for 30 min, the flask was then warmed to room temperature and 5 ml MeOH added cautiously with rigorous stirring, followed by 100 ml of ether. The ethereal solution was washed with brine and dried over MgSO4. After evaporation of the solvent, the residue was chromatographed through Florisil (250 g), eluted first with hexane and then a mixture 20% ether in hexane, giving the expected product. 4.77 g (86% yield). b.p. 92-105°/10μ.

Workup

  1. washThe ethereal solution was washed with brine
  2. dry with materialdried over MgSO4
  3. customAfter evaporation of the solvent
  4. customthe residue was chromatographed through Florisil (250 g)
  5. washeluted first with hexane

Sources & evidence

ORD record
ord-5608ceb1067d4a28808c46f0a2c1b5f8
Source dataset
uspto-grants-1980_08
Patent number
US04219489

Reaction notes

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