Triethylamine → (Z)-tert-Butyl(1-(3-chlorophenyl)but-1-enyloxy)dimethylsilane

HRID 1399543Notes

Reaction equation

HRID 1399543 reaction equation
[C:1]([Si:5]([O:8]/[C:9](/[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=[CH:10]\[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].Cl[CH:20](C)CC(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]([Cl:18])[CH:13]=1)=[CH:10]\[CH2:11][CH3:20])([CH3:7])[CH3:6])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzeneHCID 229341983-Chlorobutyrophenone

Product 1

HCID 46838070(Z)-tert-Butyl(1-(3-chlorophenyl)but-1-enyloxy)dimethylsilaneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9s was synthesized by a procedure similar to that described for 9a using 3-chlorobutyrophenone (8j, 3.1 g, 0.0169 mol), TBDMSOTf (4.3 mL, 18.6 mmol), and Et3N (3.8 mL) in CH2Cl2 (30 mL). After purification, 3.7 g (74%) of the title product was isolated as colorless oil: 1H NMR (CDCl3) δ 7.48-7.44 (m, 1H), 7.38-7.32 (m, 1H), 7.31-7.29 (m, 2H), 5.16 (t, 1H, J=7.1 Hz), 2.30-2.19 (m, 2H), 1.09-1.03 (m, 3H), 1.01 (s, 9H), −0.04 (s, 6H); 13C NMR (CDCl3) δ 147.5, 141.7, 133.9, 129.2, 127.3, 125.9, 123.8, 114.9, 25.8, 19.5, 14.1, 0.0, −4.1. C16H25ClOSi.

Workup

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

Sources & evidence

ORD record
ord-ecd7868eb7f84014a62318841fc2f2c2
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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