Sodium Hydroxide → HCID 54235402, compound

HRID 327008Notes

Reaction equation

HRID 327008 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([CH3:10])[CH3:9])[C:3]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][P:16]([CH2:22][OH:23])(=[O:21])[O:17][CH:18]([CH3:20])[CH3:19].[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Cl-].[NH4+].O>[CH3:15][P:16]([CH2:22][O:23][S:11]([C:3]1[C:4]([CH:8]([CH3:9])[CH3:10])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:12])=[O:13])(=[O:21])[O:17][CH:18]([CH3:20])[CH3:19]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 15390421HCID 15390421, compoundHCID 18981646HCID 18981646, compound

Product 1

HCID 54235402HCID 54235402, compoundYield 35.9%

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2.5 g of 2-chloro-6-isopropylbenzenesulfonyl chloride (Example 9) and 1.15 g of O-isopropyl P-methyl(hydroxymethyl)phosphinate (Example 22, Method C) dissolved in 35 ml of methylene chloride at 5° C. was added 0.23 g of benzyltriethylammonium chloride followed by 2.5 ml of 20% aqueous sodium hydroxide. The reaction mixture was allowed to warm to room temperature over 1 hour then was stirred overnight. The pale yellow mixture was diluted with saturated ammonium chloride, 25 ml, and water, 25 ml, then the layers were separated and the aqueous phase was extracted with three 50 ml portions of methylene chloride. The combined organic layers were washed with brine, dried with magnesium sulfate, filtered, and concentrated to give 3.6 of a semisolid which was flash chromatographed on silica gel using 70% ethyl acetate/30% hexanes. Similar fractions were combined to give a white solid which was recrystallized from ether and hexanes to yield 1.0 g of desired product, mp 69.5°-70.5° C.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous phase was extracted with three 50 ml portions of methylene chloride
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 3.6 of a semisolid which
  8. customchromatographed on silica gel using 70% ethyl acetate/30% hexanes
  9. customto give a white solid which
  10. customwas recrystallized from ether and hexanes

Sources & evidence

ORD record
ord-c8dc5c3ff03443cd9f1b6ef93f221927
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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