Magnesium → Tris(2-((tert-butyldimethylsilyl)oxy)benzyl)methylsilane

HRID 882556Notes

Reaction equation

HRID 882556 reaction equation
Cl[C:2]([SiH3:5])(Cl)Cl.[Si:6]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Mg]>O1CCCC1>[Si:6]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][C:2]([SiH3:5])([CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[O:13][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[O:13][Si:6]([C:9]([CH3:12])([CH3:10])[CH3:11])([CH3:8])[CH3:7])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 5462224MagnesiumHCID 13594450[2-(Bromomethyl)phenoxy](tert-butyl)dimethylsilaneHCID 71317501CID 71317501

Product 1

HCID 131732652Tris(2-((tert-butyldimethylsilyl)oxy)benzyl)methylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trichloromethylsilane (0.12 ml, 1.0 mmol) and Grignard reagent, which was prepared from 2-((tert-butyldimethylsilyl)oxy)benzyl bromide (IIa) (1.54 g, 5.0 mmol) and magnesium (1.2 g, 50 mmol) in tetrahydrofuran (12 mL), was stirred for 3 days. The reaction was quenched with satd. ammonium chloride (50 mL). The mixture was extracted with hexanes (3×50 mL). Purification by flash column chromatography (hexane/ethyl acetate=50:1, v/v) provided compound Ma (0.51 g, 72%) as a colorless oil.

Workup

  1. customThe reaction was quenched with satd
  2. extractionThe mixture was extracted with hexanes (3×50 mL)
  3. customPurification by flash column chromatography (hexane/ethyl acetate=50:1
  4. customv/v) provided compound Ma (0.51 g, 72%) as a colorless oil

Sources & evidence

ORD record
ord-66078e9c7f4b4d81b920a655481e6d12
Source dataset
uspto-grants-2015_03
Patent number
US08993804B2

Reaction notes

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