Water → HCID 14750228, compound

HRID 2073469Notes

Reaction equation

HRID 2073469 reaction equation
C([O-])(O)=[O:2].[Na+].Cl[CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][C:9]=1[CH3:24].O>CS(C)=O.C(Cl)(Cl)Cl>[CH3:24][C:9]1[CH:10]=[C:11]([CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[C:12]([CH3:14])=[CH:13][C:8]=1[CH:7]=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 14750227HCID 14750227, compound

Product 1

HCID 14750228HCID 14750228, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6212ChloroformSolvent

Procedure

DMSO (32 mL) was heated to 100° C. and then NaHCO3 (4.5 gm) was added all at once. The mixture was stirred vigorously as α-chloro-α'-diethylphosphono-2,5-dimethyl-p-xylene (7 mmol) in DMSO (45 mL) and chloroform (5 mL) was rapidly added. The mixture was stirred for 7 min. and then quickly cooled to room temperature. The reaction mixture was combined with H2O (350 mL) and extracted with 3×125 mL ethyl ether. The combined organic layers were washed with 5×150 mL H2O, dried over MgSO4, and concentrated on a rotatory evaporator to an oil. The crude material was chromatographed on silica gel (175 gm) using ethyl acetate as the eluting solvent. The appropriate fractions were pooled and concentrated to give the product as a clear oil.

Workup

  1. additionwas rapidly added
  2. extractionextracted with 3×125 mL ethyl ether
  3. washThe combined organic layers were washed with 5×150 mL H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated on a rotatory evaporator to an oil
  6. customThe crude material was chromatographed on silica gel (175 gm)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4d56948347e24accb86d23691efb7720
Source dataset
uspto-grants-1990_04
Patent number
US04918064

Reaction notes

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