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

HRID 1399544Notes

Reaction equation

HRID 1399544 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].[Si](OS(C(F)(F)F)(=O)=O)([C:22](C)(C)[CH3:23])(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][CH2:22][CH3:23])([CH3:7])[CH3:6])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

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

Product 1

HCID 46838071(Z)-tert-Butyl(1-(3-chlorophenyl)pent-1-enyloxy)dimethylsilaneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9t was synthesized by a procedure similar to that described for 9a using 3-chloropentaphenone (8k, 2.7 g, 0.014 mol), TBDMSOTf (3.5 mL, 15 mmol), and Et3N (3.1 mL) in CH2Cl2 (25 mL). After purification, 4.18 g (96%) of the title product was isolated as colorless oil: 1H NMR (CDCl3) δ 7.47-7.44 (m, 1H), 7.38-7.32 (m, 1H), 7.30-7.28 (m, 1H), 7.25-7.22 (m, 1H), 5.18 (t, 1H, J=7.2 Hz), 2.20 (q, 2H, J=7.5 Hz), 1.54-1.38 (m, 2H), 1.02 (s, 9H), 1.00-0.90 (m, 3H), −0.05 (s, 6H); 13C NMR (CDCl3) δ 148.0, 141.8, 133.9, 129.2, 127.6, 125.9, 123.9, 113.0, 28.3, 25.8, 22.8, 14.0, 0.0, −4.01. C17H27ClOSi.

Workup

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

Sources & evidence

ORD record
ord-2fd5c9ebd35443b7b949bdc4d5abff7e
Source dataset
uspto-grants-2014_12
Patent number
US08906908B2

Reaction notes

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