Methanol → HCID 24986073, compound

HRID 2055764Notes

Reaction equation

HRID 2055764 reaction equation
[CH2:1]([O:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:23]=1)[CH2:17][N:18]=[N+]=[N-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CO.[H][H]>CCOCC>[CH2:25]([O:24][C:22]1[CH:21]=[C:16]([CH:15]=[C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:23]=1)[CH2:17][NH2:18])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 887MethanolHCID 86239166HCID 86239166, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24986073HCID 24986073, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A thick walled bottle containing a stir bar was flushed out with nitrogen gas, and 5% Palladium on activated carbon (0.53 g, 10% by mass) was added along with a solution of 50% methanol and ether (approximately 10 mL). 3,5-didodecoxybenzyl azide (5.3 g, 12.6 mmol) was added using 50% methanol and ether (approximately 40 mL). The mixture was hydrogenated with hydrogen gas at 40 psi for approximately 1½ hour. The mixture was then filtered through celite with a controlled vacuum using 50% methanol and ether. The solvent was removed from the filtrate under reduced pressure and the trace solvent was removed with the high vacuum. This produced a 5.7 g yield or a 88% yield. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.87 (t, J=6.6, 8H, CH2CH3), 1.15-1.6 (m, 36H, CH2(CH2)9), 1.76 (p, J=8.0, 4H, OCH2CH2), 3.79 (s, 2H, ArCH2), 3.92 (t, J=6.6, 4H, OCH2CH2), 6.33 (t, J=2.2, 1H, ArH), 6.40 (d, J=2.2, 2H, ArH).

Workup

  1. additionA thick walled bottle containing a stir bar
  2. customwas flushed out with nitrogen gas, and 5% Palladium on activated carbon (0.53 g, 10% by mass)
  3. additionwas added along with a solution of 50% methanol and ether (approximately 10 mL)
  4. filtrationThe mixture was then filtered through celite with a controlled vacuum
  5. customThe solvent was removed from the filtrate under reduced pressure
  6. customthe trace solvent was removed with the high vacuum
  7. customThis produced a 5.7 g
  8. customyield

Sources & evidence

ORD record
ord-f5094a3a7b0d408da6ca8874b74c7879
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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