Triethylsilane → 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

HRID 556150Notes

Reaction equation

HRID 556150 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=O)=[O:5])[CH3:2].[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 248576724-(3,4-Dichlorophenyl)-1-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

Product 1

HCID 248577544-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl esterYield 97.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 9 (2.81 g, 7.74 mmol) in TFA (30 ml) was added dropwise Et3SiH (7.42 ml, 46.44 mmol) at 0° C. Stirring was continued at 0° C. for 2 hours. Then, the solvent was evaporated, and the residue was purified by chromatography, CombiFlash silica gel column, hexane/CH2Cl2, CH2Cl2 from 0% to 50%, to give compound 10 as a clear oil (mixture of cis and trans diastereomers, 2.63 g, 97%). 1H NMR (CDCl3) δ 1.18-1.34 (m, 3H), 1.88 (dd, J=25.2 Hz, 12.4 Hz) and 2.14-2.19 (m, total 1H), 2.25-2.33 (m) and 2.43-2.55 (m, total 1H), 2.67-2.74 (m) and 2.82-2.92 (m, total 1H), 3.00-3.18 (m, 2H), 4.08-4.29 (m, 3H), 6.72-7.42 (m, 7H).

Workup

  1. customThen, the solvent was evaporated
  2. customthe residue was purified by chromatography, CombiFlash silica gel column, hexane/CH2Cl2, CH2Cl2 from 0% to 50%

Sources & evidence

ORD record
ord-6a2a16bed89443d5a2fdaebd6fac4d27
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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