Sodium Hydroxide → HCID 15790542, compound

HRID 726182Notes

Reaction equation

HRID 726182 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH2:5]2.C([O:21]P(OCC)OCC)C.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)([OH:21])[CH2:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31215Triethyl phosphiteHCID 15279914HCID 15279914, compound

Product 1

HCID 15790542HCID 15790542, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of 2.4 g (0.009 moles) of the product obtained from Step B and 20 mL of toluene was added with stirring to a mixture of 1.8 g (0.010 moles) of triethylphosphite, 0.1 g (0.0004 moles) of benzyltriethyl ammonium chloride, 100 mL of toluene and 50 mL of 50% aqueous sodium hydroxide solution. A steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour. The resulting mixture was partitioned between 100 mL of Et2O and 200 mL of water and the aqueous layer was extracted with two 100 mL portions of Et2O. The combined organic layers were washed twice with 100 mL of water, twice with saturated aqueous sodium bisulfite solution, dried over MgSO4 and concentrated. The resulting crude product was chromatographed on silica gel using 2:1 hexanes-ethyl acetate to give 1.2 g of an oil that solidified on standing.

Workup

  1. additionA steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour
  2. customThe resulting mixture was partitioned between 100 mL of Et2O and 200 mL of water
  3. extractionthe aqueous layer was extracted with two 100 mL portions of Et2O
  4. washThe combined organic layers were washed twice with 100 mL of water, twice with saturated aqueous sodium bisulfite solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting crude product was chromatographed on silica gel using 2:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-2dacb3df7eaf4981ba22dc76eeddcc10
Source dataset
uspto-grants-1998_01
Patent number
US05708170

Reaction notes

Loading…