Triethylamine → 2-t-Butyl-5-(t-butyldimethylsilyloxymethyl)-1-nitrobenzene

HRID 1418177Notes

Reaction equation

HRID 1418177 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29])([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl.CCCCCC.C(OCC)C>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:27][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 193485812-t-Butyl-5-hydroxymethyl-1-nitrobenzene

Product 1

HCID 193484482-t-Butyl-5-(t-butyldimethylsilyloxymethyl)-1-nitrobenzeneYield 99.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

4.15 g (27.5 mmol) of t-butyldimethylsilyl chloride, 3.85 ml (27.6 mmol) of triethylamine and 815 mg (0.503 mmol) of 4-N,N-dimethyl-aminopyridine were added, with ice-cooling, to a solution of 5.24 g (25.0 mmol) of 2-t-butyl-5-hydroxymethyl-1-nitrobenzene (prepared as described in Preparation 10) in 50 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 40 minutes. The reaction mixture was then diluted with a 1:1 by volume mixture of hexane and diethyl ether, and the diluted solution was washed with water, with dilute aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 100 g of silica gel, using a 1:1 by volume mixture of methylene chloride and hexane as the eluent, to give 8.04 g (yield 99%) of the title compound as an oily substance.

Workup

  1. washthe diluted solution was washed with water, with dilute aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  2. customThe solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through 100 g of silica gel
  4. additionby volume mixture of methylene chloride and hexane as the eluent

Sources & evidence

ORD record
ord-678a39e062804ed8a8ad0d70954ed814
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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