Triethylamine → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

HRID 1418050Notes

Reaction equation

HRID 1418050 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:16]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

At room temperature, 10.9 g of 4-pyridylcarbinol (100 mmol) was treated with 60 mL of DCM followed by 21 mL (150 mmol) of triethylamine. After being cooled to 10° C., 18 g (120 mmol) of t-butyldimethylsilyl chloride (dissolved in 20 mL DCM) was added dropwise. The resulting reaction mixture was warmed to room temperature slowly and stirred overnight. Subsequently, it was filtered over a pad of celite, rinsed with ether. Volatiles were removed and the residue was taken up in hexane and filtered over celite again, washed with hexane/ether, and the solvents removed by rotoevaporation. This was repeated twice. Pumping under high vac of the residue thus obtained provided 22 g (99%) of the desired product as a light brown oil, mass spectrum (CI) m/e=224 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to room temperature slowly
  3. filtrationSubsequently, it was filtered over a pad of celite
  4. washrinsed with ether
  5. customVolatiles were removed
  6. filtrationfiltered over celite again
  7. washwashed with hexane/ether
  8. customthe solvents removed by rotoevaporation
  9. customthus obtained

Sources & evidence

ORD record
ord-782d45c29d234e9288c1599a5b0250cf
Source dataset
uspto-grants-1999_03
Patent number
US05880139

Reaction notes

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