Tetrahydrofuran → HCID 11989423, compound

HRID 2423271Notes

Reaction equation

HRID 2423271 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][SiH2:2]1.[C:6]1([Mg]Br)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:14]1[CH2:18]O[CH2:16][CH2:15]1>C(OCC)C>[OH:1][CH2:5][C:4]1[CH:18]=[CH:14][CH:15]=[CH:16][C:3]=1[Si:2]([CH:9]([CH3:10])[CH3:8])([CH:6]([CH3:11])[CH3:7])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 123209143HCID 123209143, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 11989423HCID 11989423, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The resultant oxasilacyclopentane (11.0 g, 50.0 mmol) was dissolved in THF (125 ml), and a 1.07M solution of phenylmagnesium bromide in THF (51 ml, 55 mmol) was slowly added thereto at 0° C. After finishing dropping the solution, the resultant was stirred at room temperature for 16 hours. The reaction solution was diluted with diethyl ether and was washed with a saturated NH4Cl aqueous solution, water, and brine, and then was dried over anhydrous MgSO4. After removal of the solvents, the residue was purified by column chromatography on silica gel, thereby obtaining [2-(hydroxymethyl)phenyl]diisopropylphenylsilane (13.5 g, 90%) as colorless crystal.

Workup

  1. customat 0° C
  2. washwas washed with a saturated NH4Cl aqueous solution, water, and brine
  3. dry with materialwas dried over anhydrous MgSO4
  4. customAfter removal of the solvents
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f9ece0119fdb4c768bf8d62d9477fef5
Source dataset
uspto-grants-2011_06
Patent number
US07960571B2

Reaction notes

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