Triethylamine → HCID 86747148, compound

HRID 2255126Notes

Reaction equation

HRID 2255126 reaction equation
[Br:1]C[C:3]1[C:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][OH:18].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28].[CH3:34]N(C1C=CC=CN=1)C>ClCCl>[Br-:1].[CH3:16][C:13]([Si:10]([CH3:11])([CH3:12])[O:9][C:8]1[CH:3]=[C:4]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:5]=[CH:6][C:7]=1[CH2:34][N+:29]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:27][CH3:28])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 86747149HCID 86747149, compound

Product 1

HCID 86747148HCID 86747148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(bromomethyl-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzenemethanol (6.35 g, 19.2 mmol) from Preparation 15, tert-butyldimethylsilyl chloride (4.3 g, 28.8 mmol), triethylamine (5.3 mL, 38.3 mmol), and dimethylaminopyridine (90 mg) in dichloromethane (50 mL) is stirred at room temperature for 24 hours. Dichloromethane (1 L) is added and the organic phase washed with H2O 100 mL). The organic phase is dried (MgSO4) and concentrated. The residue is purified by silica gel chromatography (2.5% MeOH/CH2Cl2 followed by 5% MeOH/CHCl2). A yellow-orange solid of 2-[[(1,1-dimethylethyl)dimethylsilyl]-oxy]-4-[[[(1,1-dimethylethyl) dimethylsilyl]oxy]-methyl]-N,N,N-triethylbenzenemethanaminium bromide is obtained (7.68 g, 73%).

Workup

  1. washthe organic phase washed with H2O 100 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel chromatography (2.5% MeOH/CH2Cl2 followed by 5% MeOH/CHCl2)

Sources & evidence

ORD record
ord-23abe932edf749eca257b1af6ef45f87
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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