Pyridine → 160701-58-6

HRID 1241338Notes

Reaction equation

HRID 1241338 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][OH:7].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl>[C:14]([Si:11]([CH3:13])([CH3:12])[O:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:6][OH:7])[CH:8]=[CH:9][CH:10]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 834043-Hydroxyphenethyl alcohol

Product 1

HCID 10800835160701-58-6Yield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxyphenethyl alcohol (6.0 g, 43.4 mmol) in 275 mL of CH2Cl2 was added 6.55 g (43.4 mmol) of TBDMS-Cl (tert-butyldimethylsilyl chloride), cooled to 0° C., then added 7.0 mL (86.8 mmol) of pyridine. The reaction mixture was stirred at ambient temperature overnight. Upon concentration, the crude mixture was purified by silica gel flash chromatography (eluted with hexane then 5% EtOAc/hexane) to provide 8.9 g of a clear oil: 1H NMR (300 MHz, DMSO-d6) δ 9.17 (s, 1H), 7.04 (m, 1H), 6.60 (m, 3H), 3.73 (t, J=6.9 Hz, 2H), 2,65 (t, J=6.9 Hz, 2H), 0.83 (s, 9H), −0.03 (s, 6H).

Workup

  1. concentrationUpon concentration
  2. customthe crude mixture was purified by silica gel flash chromatography (
  3. washeluted with hexane

Sources & evidence

ORD record
ord-275df6e1484c4b8abed541f2e9d79fa0
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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