Diethyl Ether → 2-Trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate

HRID 481226

Reaction equation

HRID 481226 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[CH:5]=[CH:4][C:3]1=2.O[C:22]1[CH:36]=[CH:35][C:25]([C:26]([O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])=[O:27])=[CH:24][CH:23]=1.Cl.CN(C)CCCN=C=NCC.CCOCC>CN(C=O)C>[CH3:32][Si:31]([CH3:34])([CH3:33])[CH2:30][CH2:29][O:28][C:26](=[O:27])[C:25]1[CH:35]=[CH:36][C:22]([O:18][C:17]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:20])([CH3:1])[CH2:11][CH:10]=[C:9]([C:12]4[S:13][CH:14]=[CH:15][CH:16]=4)[C:8]=3[CH:7]=2)=[O:19])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107081975,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid2×HCID 108475492-Trimethylsilylethyl 4-hydroxybenzoate

Product 1

HCID 106016292-Trimethylsilylethyl 4-[[(5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalen-2-yl)carbonyl]oxy]-benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid (Compound E6, 79.0 mg, 0.280 mmol), 2-trimethylsilylethyl 4-hydroxybenzoate (73.3 mg, 0.308 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (70.0 mg, 0.364 mmol), and 4-N,N-dimethylaminopyridine (44.5 mg, 0.364 mmol) in 2.0 mL DMF was stirred overnight at room temperature. Et2O (100 mL) was added and the solution washed with H2O, 5% HCl, saturated aqueous NaCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the sovents under reduced pressure and column chromatography (10% EtOAc-hexanes) of the residual oil afforded the title compound as a colorless solid.

Workup

  1. washthe solution washed with H2O, 5% HCl, saturated aqueous NaCO3, and saturated aqueous NaCl
  2. dry with materialbefore being dried over MgSO4
  3. customRemoval of the sovents under reduced pressure and column chromatography (10% EtOAc-hexanes) of the residual oil

Sources & evidence

ORD record
ord-1232509fe7354c449fdb00d6c6f22c92
Source dataset
uspto-grants-2003_11
Patent number
US06653483B1

Linked notes

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