Water → HCID 56626090, compound

HRID 1906961Notes

Reaction equation

HRID 1906961 reaction equation
[CH2:1]([Li])CCC.[CH2:6]1[O:16][CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]#C)[O:8][CH2:7]1.[C:17]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)([O:19][CH3:20])=[O:18].O>CCOCC>[CH2:7]1[O:8][C:9]([CH3:1])([CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH:25]([C:24]2[CH:27]=[CH:28][C:21]([C:17]([O:19][CH3:20])=[O:18])=[CH:22][CH:23]=2)[OH:26])[O:16][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 56620052HCID 56620052, compoundHCID 178418339Butyllithium

Product 1

HCID 56626090HCID 56626090, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyl-lithium (1 equivalent) was added dropwise under nitrogen to a solution of heptan-1-yne-7-one ethylene ketal (5.0 g) in ether at ice salt temperature and gave an intense red colour. The solution was stirred at this temperature for 40 minutes. This solution was added to a solution of 4-carbomethoxybenzaldehyde (5.3 g) at the same temperature and produced a grey precipitate. The mixture was left to warm to room temperature. Water was added, the layers separated and the ether layer dried (MgSO4). Removal of the solvent gave an oil which was chromatographed on silica (300 g). Elution with ether gave 1-(4-carbomethoxyphenyl)-1-hydroxyoctan-2-yne-7-one ethylene ketal as a clear oil (5 g). τ (CDCl3) 8.77 (3H, s), 8.35 (4H, m), 7.75 (2H, t, J=7 Hz), 6.85 (1H, broad), 6.16 (3H, s+4H, s), 4.52 (1H, s), 2.45 (2H, d, J=8 Hz), 2.0 (2H, d, J=8 Hz).

Workup

  1. customgave an intense red colour
  2. customproduced a grey precipitate
  3. waitThe mixture was left
  4. customthe layers separated
  5. dry with materialthe ether layer dried (MgSO4)
  6. customRemoval of the solvent
  7. customgave an oil which
  8. customwas chromatographed on silica (300 g)
  9. washElution with ether

Sources & evidence

ORD record
ord-3491f8d779684c03b93e67b3cdf01902
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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