Hydrochloric Acid → HCID 22313341, compound

HRID 965844Notes

Reaction equation

HRID 965844 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:11]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[OH:23])[C:16]([O:18][CH3:19])=[O:17])=O.Cl>C1COCC1>[OH:23][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[CH:11]=[CH2:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 22313341HCID 22313341, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran) (8 mL) in a 0° C. ice bath is added methyl triphenylphonium bromide (1.92 g, 5.38 mmol). The mixture is allowed to warm to rt and stir for 10 min. A solution of methyl 3-formyl-4-hydroxybenzoate (200 mg, 1.11 mmol) in THF (3 mL) is added to the above solution. The mixture is stirred at rt for 5 h. The reaction mixture is acidified to pH=5 with 1N HCl, and extracted with ether (3×). The combined organic layers are washed with brine, dried (MgSO4), filtered and concentrated to a yellow oil. The crude product is purified by chromatography on SiO2. Elution with hexanes-EtOAc (80:20) gives 130 mg (66%) of methyl 4-hydroxy-3-vinylbenzoate as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.12, 7.86, 6.93, 6.85, 5.84, 5.50, 5.46, 3.92.

Workup

  1. stirringThe mixture is stirred at rt for 5 h
  2. extractionextracted with ether (3×)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow oil
  7. customThe crude product is purified by chromatography on SiO2
  8. washElution with hexanes-EtOAc (80:20)

Sources & evidence

ORD record
ord-a6d358129838419a8efe462ffb09b575
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

Loading…