Triethylamine → (Z)-tert-Butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilane

HRID 1399539Notes

Reaction equation

HRID 1399539 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].[F: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:17]=[CH:16][CH:15]=[C:14]([F:19])[CH:13]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzeneHCID 122317123-Fluoro-1-phenylpropan-1-one

Product 1

HCID 46837928(Z)-tert-Butyl(1-(3-fluorophenyl)prop-1-enyloxy)dimethylsilaneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9c was synthesized by a procedure similar to that described for 9a using commercially available 3-fluoropropiophenone (8c, 5.0 g, 0.033 mol), TBDMSOTf (8.3 mL, 36.1 mmol), and Et3N (7.3 mL) in CH2Cl2 (50 mL). After purification, 8.1 g (93%) of 9c was isolated as colorless oil: 1H NMR (CDCl3) δ 7.38-7.10 (m, 2H), 7.00-6.87 (m, 1H), 5.26 (q, 1H, J=6.9 Hz), 1.75 (d, 3H, J=6.9 Hz), 1.00 (s, 9H), −0.02 (s, 6H); 13C NMR (CDCl3) δ 164.5, 161.2, 149.2, 142.4, 129.4, 121.4, 114.3, 114.0, 112.8, 112.5, 107.1, 105.9, 26.0, 18.5, 11.9, −3.9. C15H23FOSi.

Workup

  1. customCompound 9c was synthesized by a procedure similar to
  2. customAfter purification

Sources & evidence

ORD record
ord-d912e56409164ad6a565a1224a8a2ae8
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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