Cyclohexene → 5-Hydroxymethyl-2-trimethylsilyl-furo[2,3-c]pyridine

HRID 1072979Notes

Reaction equation

HRID 1072979 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH2:15][OH:16])[CH:5]=[C:6]2[CH:10]=[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]=12.C1CCCCC=1>[Pd].CCO>[OH:16][CH2:15][C:4]1[CH:5]=[C:6]2[CH:10]=[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]2=[CH:2][N:3]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 22047422[7-Chloro-2-(trimethylsilyl)furo[2,3-c]pyridin-5-yl]methanol

Product 1

HCID 220472255-Hydroxymethyl-2-trimethylsilyl-furo[2,3-c]pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

C5 (1.05 g, 4.1 mmol) and 10% Pd/C catalyst (1.05 g) are placed in 20 mL absolute EtOH. Cyclohexene (4 mL, 40.1 mmol) is added, and the reaction is refluxed for 2.5 h, and then filtered through celite. The filter cake is washed with 1:1 EtOH/CH2Cl2, and the filtrate is concentrated to a pale yellow solid. The residue is partitioned between 40 mL saturated NaHCO3 and extracted with CH2Cl2 (4×20 mL). The combined organic layer is dried over MgSO4, filtered, and then concentrated in vacuo to a pale oil (1.04 g). The pale oil is chromatographed over 50 g silica gel (230-400 mesh) eluting with 50-70% EtOAc/hexane to afford 5-hydroxymethyl-2-trimethylsilyl-furo[2,3-c]pyridine (C14) as a white solid (90% yield). MS (EI) for C11H15NO2Si, m/z: 221(M)+.

Workup

  1. temperaturethe reaction is refluxed for 2.5 h
  2. filtrationfiltered through celite
  3. washThe filter cake is washed with 1:1 EtOH/CH2Cl2
  4. concentrationthe filtrate is concentrated to a pale yellow solid
  5. customThe residue is partitioned between 40 mL saturated NaHCO3
  6. extractionextracted with CH2Cl2 (4×20 mL)
  7. dry with materialThe combined organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo to a pale oil (1.04 g)
  10. customThe pale oil is chromatographed over 50 g silica gel (230-400 mesh)
  11. washeluting with 50-70% EtOAc/hexane

Sources & evidence

ORD record
ord-c4e4e3a84f4c4dd88c99e4bd7570c7be
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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