Benzoyl Peroxide → HCID 86599573, compound

HRID 855066Notes

Reaction equation

HRID 855066 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12](OC(N3C=CN=C3)=S)[C:13]([F:16])([F:15])[F:14])[CH:11]=1)[O:8][CH:7]([C:25]([F:28])([F:27])[F:26])[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5]2.[SiH](CC)(CC)CC.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][C:13]([F:14])([F:15])[F:16])[CH:11]=1)[O:8][CH:7]([C:25]([F:28])([F:26])[F:27])[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5]2

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 12052TriethylsilaneHCID 86599574HCID 86599574, compound

Product 1

HCID 86599573HCID 86599573, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The ester from Step 1 (2.1 g, 4.25 mmol) was dissolved in toluene (15 mL). The Et3SiH (30 mL, 0.18 mol) was added to above solution. The mixture was heated to reflux. The benzoyl peroxide (1.03 g, 4.25 mmol) in toluene (15 mL) was added in 4 portions at 15 min intervals. The mixture was heated to reflux for 2 hours and stirred at r.t overnight. The mixture was passed through silic plug and plug was washed with 5% to 10% EtOAc in hexane to give crude product: LCMS m/z 369.15 (M+H). This ester was of suitable purity to use without further purification.

Workup

  1. temperatureThe mixture was heated to reflux
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 2 hours
  4. washwas washed with 5% to 10% EtOAc in hexane
  5. customto give crude product
  6. customto use without further purification

Sources & evidence

ORD record
ord-7a04a4e43e954619877efea1efcc353a
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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