Allylchlorodimethylsilane → tert-butyl-N-{4-[allyl(dimethyl)silyl]-2-ethoxyphenyl}carbamate

HRID 1292835Notes

Reaction equation

HRID 1292835 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=1[O:15][CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].[H-].[K+].C([Li])(C)(C)C.[CH2:26]([Si:29](Cl)([CH3:31])[CH3:30])[CH:27]=[CH2:28].C(OC(=O)NC1C=CC([Si](CC=C)(C)C)=CC=1OC)(C)(C)C>CCCCCC>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([Si:29]([CH2:26][CH:27]=[CH2:28])([CH3:31])[CH3:30])=[CH:10][C:9]=1[O:15][CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 77646AllylchlorodimethylsilaneHCID 82127Potassium hydrideHCID 15414577tert-butyl-N-{4-[allyl(dimethyl)silyl]-2-methoxyphenyl}carbamateHCID 58904628tert-butyl N-(4-bromo-2-ethoxyphenyl)carbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 58904655tert-butyl-N-{4-[allyl(dimethyl)silyl]-2-ethoxyphenyl}carbamateYield 58.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The reaction between 5.3 g (16.8 mmol) of tert-butyl-N-(4-bromo-2-ethoxyphenyl)carbamate 5, 2.4 g (20.16 mmol, 1.2 eq) of 35% potassium hydride, 20.2 ml (34.4 mmol, 2.05 eq) of 1.5 M tert-butyllithium in hexane and 6 ml (40.3 mmol, 2.4 eq) of allyl(chloro)dimethylsilane according to the procedure described for compound 6, followed by two successive purifications by column chromatography (eluant petroleum ether/AcOEt 9:1), lead to 3.3 g of a colorless oil (yield: 58%).

Sources & evidence

ORD record
ord-5e24b01100684618b6fd26dd48178531
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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