Tetrahydrofuran → HCID 12058650, compound

HRID 1287967Notes

Reaction equation

HRID 1287967 reaction equation
[Li].[C:2]1([P:8](Cl)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:22]=[CH:21][C:20]([Si:23]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH:19][CH:18]=1.[O:33]1CCCC1>>[C:2]1([P:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:17]2[CH:22]=[CH:21][C:20]([Si:23]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH:19][CH:18]=2)=[O:33])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 66180ChlorodiphenylphosphineHCID 3028194LithiumHCID 13033313HCID 13033313, compound

Product 1

HCID 12058650HCID 12058650, compoundYield 68.1%

Procedure

To the lithium diphenylphosphide solution prepared under nitrogen from lithium (0.6246 g, 0.09 g atom) and diphenylphosphinous chloride (9.92 g, 0.045 mol) in 50 ml dry tetrahydrofuran, 14.5 g (0.045 mol) of 4-bromophenyl triethoxysilane dissolved in 50 ml dry tetrahydrofuran is added during one hour. The blood-red solution turns to a light brown color with the appearance of a small amount of white solid. The solution is filtered under nitrogen, diluted with benzene to precipitate remaining lithium bromide, and refiltered. Analysis of the solution by gasliquid chromatography shows a content of unreacted bromosilane of 3.88 grams (0.0122 mol). Distillation in vacuum gives 4-(diphenylphosphinyl)phenyl triethoxysilane (13 grams, 68.1 percent yield), b.p. 164°-167° C/0.1 mm. The H'NMR spectrum is identical to the material prepared from 4-(diphenylphosphinyl)phenyl magnesium bromide and tetraethyl orthosilicate. The efficiency based upon bromosilane consumed is 93.4 percent.

Workup

  1. additionis added during one hour
  2. filtrationThe solution is filtered under nitrogen
  3. additiondiluted with benzene
  4. customto precipitate
  5. distillationDistillation in vacuum

Sources & evidence

ORD record
ord-e49b847683304c9f958817f67752c3a3
Source dataset
uspto-grants-1976_10
Patent number
US03987009

Reaction notes

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