Hydrogen Peroxide → HCID 68851729, compound

HRID 858976Notes

Reaction equation

HRID 858976 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH3:13][C:14]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:15]=1[C:16](Cl)=[O:17].[CH3:25][O:26][CH2:27][CH2:28][N:29]([CH2:37][CH2:38][O:39][CH3:40])[C:30]1[CH:35]=[CH:34][C:33]([PH2:36])=[CH:32][CH:31]=1.[OH:41]O.[O:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1>>[CH3:44][C:45]1[CH:1]=[C:2]([CH3:3])[CH:12]=[C:10]([CH3:11])[C:46]=1[C:47]([P:36](=[O:41])([C:16](=[O:17])[C:15]1[C:14]([CH3:13])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=1[CH3:24])[C:33]1[CH:34]=[CH:35][C:30]([N:29]([CH2:37][CH2:38][O:39][CH3:40])[CH2:28][CH2:27][O:26][CH3:25])=[CH:31][CH:32]=1)=[O:43]

Participants

7

Reactant 6

HCID 784Hydrogen PeroxideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 68853866HCID 68853866, compoundHCID 178418339Butyllithium

Product 1

HCID 68851729HCID 68851729, compound

Procedure

200 ml (0.332 mol; 1.6M) of butyllithium are added dropwise at 0° C., under argon, in the course of 30 minutes to a solution of 33.6 g (0.332 mol) of diisopropylamine in 100 ml of tetrahydrofuran. The resulting solution is added dropwise at −20° C. in the course of 2 hours to a solution of 60.6 g (0.332 mol) of 2,4,6-trimethylbenzoyl chloride and 36.4 g (0.151 mol) of 4-[bis(2-methoxy-ethyl)amino]-phenyl-phosphine (prepared as described in Example 1) in 200 ml of tetrahydrofuran. After 2 hours' stirring, the yellow reaction solution is heated to room temperature and the solvent is removed using a rotary evaporator. The residue is taken up in 200 ml of toluene and washed once with water. 17.1 g (0.151 mol; 30%) of hydrogen peroxide are added to the organic phase. After 2 hours' stirring, washing is carried out first with water, then with saturated sodium hydrogen carbonate solution. Drying is then carried out with magnesium sulfate, followed by filtration and concentration using a rotary evaporator. After crystallisation from isopropanol, 30.2 g (36.4% of theory) of the title compound are obtained in the form of a yellow powder having a melting point of 103–106° C. (31P-NMR 10.23 ppm).

Workup

  1. customthe solvent is removed
  2. customa rotary evaporator
  3. washwashed once with water
  4. stirringAfter 2 hours' stirring
  5. washwashing
  6. customDrying
  7. filtrationfollowed by filtration and concentration
  8. customa rotary evaporator
  9. customAfter crystallisation from isopropanol, 30.2 g (36.4% of theory) of the title compound
  10. customare obtained in the form of a yellow powder

Sources & evidence

ORD record
ord-c2da5930e5c84053b1325e8a6a2fc73c
Source dataset
uspto-grants-2006_12
Patent number
US07148382B2

Reaction notes

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