Triethylamine → 6[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-naphthalenecarboxylic acid, methyl ester

HRID 1512188Notes

Reaction equation

HRID 1512188 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.Cl[Si:24]([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:40][C:37]([Si:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5]2)([CH3:38])[CH3:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 11367671Methyl 6-hydroxy-1-naphthoate

Product 1

HCID 866414066[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-1-naphthalenecarboxylic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6-hydroxy-1-naphthalenecarboxylic acid, methyl ester (1.01 g, 5 mmol), triethylamine (1.55 mL, 6 mmol) and N,N-dimethyl-4-pyridineamine (0.30 g, 2.5 mmol) in CH2Cl2 (25 mL) is treated with a solution of chloro(1,1-dimethylethyl)diphenylsilane (1.55 mL, 6 mmol) in CH2Cl2 (10 mL) and stirred at room temperature overnight. The mixture is washed with saturated aqueous NaHCO3, dried (Na2SO4) and solvent is evaporated off under reduced pressure to give a residue, which is purified by column chromatography (SiO2; hexane/CH2Cl2 1:1) to afford the title compound as an oil.

Workup

  1. washThe mixture is washed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4) and solvent
  3. customis evaporated off under reduced pressure
  4. customto give a residue, which
  5. customis purified by column chromatography (SiO2; hexane/CH2Cl2 1:1)

Sources & evidence

ORD record
ord-3557be3f2d3444efbb9a24b12126e7b3
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

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