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

HRID 1399542Notes

Reaction equation

HRID 1399542 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].[N+:19](CCC(C1C=CC=CC=1)=O)([O-:21])=[O:20].[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]([N+:19]([O-:21])=[O:20])[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 5694913-Nitro-1-phenylpropan-1-oneHCID 113005611-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene

Product 1

HCID 46838067(Z)-tert-Butyl-(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilaneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9g was synthesized by a procedure similar to that described for 9a using commercially available 3-nitropropiophenone (8g, 5.0 g, 0.028 mol), TBDMSOTf (7.1 mL, 30.7 mmol), and Et3N (6.2 mL) in CH2Cl2 (50 mL). After purification on alumina, 8.0 g (98%) of 9g was isolated as colorless oil: 1H NMR (CDCl3) δ 8.34-8.30 (m, 1H), 8.12-8.06 (m, 1H), 7.80-7.75 (m, 1H), 7.52-7.42 (m, 1H), 5.40 (q, 1H, J=6.9 Hz), 1.78 (d, 3H, J=6.9 Hz), 1.02 (s, 9H), −0.02 (s, 6H); 13C NMR (CDCl3) δ 148.8, 141.6, 131.3, 129.0, 122.1, 120.5, 108.6, 106.8, 25.9, 18.4, 12.0, −3.8. C15H23NO3Si.

Workup

  1. customCompound 9g was synthesized by a procedure similar to
  2. customAfter purification on alumina

Sources & evidence

ORD record
ord-77fc56394ec24c3fae07a07a5b4450b8
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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