Triethylamine → Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 1440459Notes

Reaction equation

HRID 1440459 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 64212496-Bromo-3-pyridinemethanol

Product 1

HCID 6425754Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-Yield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-bromo-5-hydroxymethylpyridine (4.7 g, 0.023 mol) and triethylamine (3.4 mL, 0.024 mol) in DMF (30 mL) was added tert-butyldimethylsilyl chloride. After 1 h, the mixture was diluted with ether and washed with water. The ether phase was dried (MgSO4) and concentrated to give 6.8 g (97%) of product as a colorless oil.

Workup

  1. washwashed with water
  2. dry with materialThe ether phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b5722111615948fca36af1b01a8c4aec
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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