Chlorotrimethylsilane → HCID 11046597, compound

HRID 1587464Notes

Reaction equation

HRID 1587464 reaction equation
[CH2:1]([PH:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)Cl.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[C:29]=1[C:30](Cl)=[O:31]>O1CCCC1>[CH2:1]([P:8](=[O:13])([CH2:9][CH2:10][CH2:11][CH3:12])[C:30](=[O:31])[C:29]1[C:28]([O:27][CH3:26])=[CH:36][CH:35]=[CH:34][C:33]=1[O:37][CH3:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 748102,6-Dimethoxybenzoyl chlorideHCID 178454900HCID 178454900, compound

Product 1

HCID 11046597HCID 11046597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 13.2 g (0.067 mol) of benzyl-butylphosphin oxide and 12.7 ml (0.101 mol) of trimethylchlorosilane in 100 ml of tetrahydrofuran are added 18.7 ml (0.134 mol) of triethylamine under a nitrogen atmosphere at 0°-5° C. in the course of 15 minutes. After 2 hours of stirring at 0°-5° C., 13.5 g (0.067 mol) of 2,6-dimethoxybenzoyl chloride, diluted in 50 ml of tetrahydrofuran, are added during the course of 20 min. the stirring at 0°-5° C. is continued for 2 h, then the solution is allowed to warm to room temperature and filtered over silicea gel. The solution is concentrated in vacuo and the residue recrystallized from a hexan/acetic acid ester mixture. 3.8 g (15.8% of theory) of the title compound with a melting point of 56°-57° C. are obtained.

Workup

  1. additionare added during the course of 20 min. the stirring at 0°-5° C.
  2. waitis continued for 2 h
  3. filtrationfiltered over silicea gel
  4. concentrationThe solution is concentrated in vacuo
  5. customthe residue recrystallized from a hexan/acetic acid ester mixture

Sources & evidence

ORD record
ord-e32d4afb09fd4e78879e1bb08eadac56
Source dataset
uspto-grants-1993_06
Patent number
US05218009

Reaction notes

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