Tetraethoxysilane → HCID 21503214, compound

HRID 1287966Notes

Reaction equation

HRID 1287966 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Mg].[Si:22](OCC)([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>O1CCCC1>[CH2:24]([O:23][Si:22]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])[C:2]1[CH:7]=[CH:6][C:5]([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 69773(4-Bromophenyl)diphenylphosphineHCID 5462224Magnesium

Product 1

HCID 21503214HCID 21503214, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a Grignard reagent solution prepared from 4-bromophenyl diphenylphosphine (36 g, 0.1 mol) and magnesium (2.43 g, 0.10 g atom) in 130 ml of dry tetrahydrofuran, tetraethyl orthosilicate (54 g, 0.21 mol) is added and the solution heated at 55° C for 4 hours. The solvent is removed in vacuum leaving 27 grams of clear liquid, analyzing 50 percent product by gas-liquid chromatography. A sample separated by this means gave a H'NMR, delta (C6D6): 8.84 (t, 9H); 3.74 (q, 6H); 6.90-7.90 (m, 14H), consistent with the structure expected. The yield is 32 percent.

Workup

  1. additionis added
  2. customThe solvent is removed in vacuum

Sources & evidence

ORD record
ord-c09c54e92c9e4baa88d763bb2429fe93
Source dataset
uspto-grants-1976_10
Patent number
US03987009

Reaction notes

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