Triethylamine → (Z)-tert-Butyl(1-(m-tolyl)prop-1-enyloxy)dimethylsilane

HRID 1399541Notes

Reaction equation

HRID 1399541 reaction equation
[C:1]([Si:5]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14](Cl)[CH:13]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:19]CCC(C1C=CC=CC=1)=O.[Si](OS(C(F)(F)F)(=O)=O)(C(C)(C)C)(C)C.CCN(CC)CC>C(Cl)Cl>[C:1]([Si:5]([O:8]/[C:9](/[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[CH:16][CH:17]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10315ButyrophenoneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene

Product 1

HCID 46838065(Z)-tert-Butyl(1-(m-tolyl)prop-1-enyloxy)dimethylsilaneYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9e was synthesized by a procedure similar to that described for 9a using commercially available 3-methylpropiophenone (8e, 5.0 g, 0.033 mol), TBDMSOTf (8.5 mL, 36.1 mmol), and Et3N (7.5 mL) in CH2Cl2 (50 mL). After purification by column chromatography on silica gel, 7.45 g (84%) of 9e was isolated as colorless oil: 1H NMR (CDCl3) δ 7.31-7.24 (m, 2H), 7.23-7.17 (m, 1H), 7.10-7.05 (m, 1H), 5.22 (q, 1H, J=6.9 Hz), 2.37 (s, 3H), 1.76 (d, 3H, J=6.9 Hz), 1.03 (s, 9H), −0.03 (s, 6H); 13C NMR (CDCl3) δ 150.7, 140.1, 137.7, 128.4, 127.9, 126.8, 123.2, 105.9, 26.3, 21.8, 18.7, 12.1, −3.6. C16H26OSi.

Workup

  1. customCompound 9e was synthesized by a procedure similar to
  2. customAfter purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-b96301f933764b21bc62bc296fbde524
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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