Pyridine → HCID 58352682, compound

HRID 39259Notes

Reaction equation

HRID 39259 reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][CH2:9][NH:10][C:11](=[O:24])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[CH:8]([CH2:9][NH:10][C:11](=[O:24])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=1)=[O:7]

Participants

5

Reactant 2

HCID 1049PyridineHCID 583526384-Acetoxybenzyl 2-hydroxyethylcarbamate

Product 1

HCID 58352682HCID 58352682, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridine (1.15 mL) in 20 mL of CH2Cl2 was cooled in an ice bath and chromium trioxide (711 mg) was added in one portion. The mixture was stirred at the same temperature for 5 min and at room temperature for 1 h. A solution of 62 (300 mg, 1.18 mmol) in 10 mL of CH2Cl2 was added in one portion and the mixture was stirred for 45 min at room temperature. The solution was decanted, diluted with 100 mL of CH2Cl2 and washed with aqueous NaHCO3 (2×75 mL), saturated NaCl (1×75 mL), dried over Na2SO4, filtered and concentrated in vacuo to give the crude aldehyde which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 2.20 (s, 3H), 4.03 (s, 2H), 5.0 (s, 2H), 5.42 (broad s, 1H), 6.97 (d, J=8.5 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 9.56 (s, 1H).

Workup

  1. stirringthe mixture was stirred for 45 min at room temperature
  2. customThe solution was decanted
  3. additiondiluted with 100 mL of CH2Cl2
  4. washwashed with aqueous NaHCO3 (2×75 mL), saturated NaCl (1×75 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25e4883a59c34896852ebbae16efffe5
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

Loading…