Triethylamine → HCID 14548451, compound

HRID 1904510Notes

Reaction equation

HRID 1904510 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([P:15](=O)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)([O:3][CH3:4])=[O:2].C(N(CC)CC)C.Cl[SiH](Cl)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:11]([C:9]1[CH:8]=[C:7]([P:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[C:5]([C:1]([O:3][CH3:4])=[O:2])[CH:10]=1)([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 10692002HCID 10692002, compound

Product 1

HCID 14548451HCID 14548451, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 17.0 g (4.31×10-2 mol) of 3,5-dicarbomethoxyphenyldiphenylphosphine oxide (from Preparation 3), 4.71 g (4.65×10-2 mol) of triethylamine and 196 ml of dry toluene under nitrogen was added 6.76 g (4.74×10-2 mol) of trichlorosilane. The mixture was then heated at reflux for 15.25 hr and cooled. A solution of 20% sodium hydroxide (49 ml) was added and the mixture was stirred. The organic layer was separated, washed with two 250 ml portions of water, dried over MgSO4 and concentrated to an oil which crystallized. The solid was recrystallized twice from methanol and dried. The yield of 3,5-dicarbomethoxyphenyldiphenylphosphine was 14.0 g (85.8% of theory); mp=103-4.5° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 15.25 hr
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed with two 250 ml portions of water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to an oil which
  8. customcrystallized
  9. customThe solid was recrystallized twice from methanol
  10. customdried

Sources & evidence

ORD record
ord-b9f17a1260544e3aa298e0119c4a1b42
Source dataset
uspto-grants-1989_06
Patent number
US04837394

Reaction notes

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