Iodine → (3-Ethoxypropyl)diisopropylsilane

HRID 1169569Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH3:7].[Mg].II.[CH:11]([SiH:14]([CH:16]([CH3:18])[CH3:17])Cl)([CH3:13])[CH3:12].[Cl-].[NH4+]>C1COCC1>[CH2:6]([O:5][CH2:4][CH2:3][CH2:2][SiH:14]([CH:16]([CH3:18])[CH3:17])[CH:11]([CH3:13])[CH3:12])[CH3:7]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Bromo-3-ethoxypropane (5.85 g, 35.0 mmol) was dissolved in THF (30 mL). Magnesium (900 mg, 37.0 mmol) and iodine (catalytic amount) were added thereto, and the resultant mixture was stirred at room temperature for 30 minutes and at 60° C. for 10 minutes. The resultant mixture was added dropwise to diisopropylchlorosilane (5.12 mL, 30.0 mmol) in THF (40 mL), followed by stirring at room temperature for 15 minutes and at 60° C. for 1.5 hours. Saturated aqueous ammonium chloride was added thereto, and the resultant mixture was extracted with pentane, followed by washing with water six times and drying over sodium sulfate anhydrate. The solvent was removed under reduced pressure, whereby the Compound 61a was obtained as an yellow liquid (6.52 g, 92%).

Workup

extractionthe resultant mixture was extracted with pentane
washby washing with water six times
dry with materialdrying over sodium sulfate anhydrate
customThe solvent was removed under reduced pressure, whereby the Compound 61a

Sources & evidence

ORD record: ord-4713cfaf08d949ef970c4be7798a0db9
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825103B2

Reaction notes

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