Water → 4-Methoxybenzoic acid, 6-aminohexyl ester

HRID 324109Notes

Reaction equation

HRID 324109 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:8])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 865836674-Methoxybenzoic acid, 6-azidohexyl ester

Product 1

HCID 572173864-Methoxybenzoic acid, 6-aminohexyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxybenzoic acid, 6-azidohexyl ester (1.119 g, 4.035 mmol), triphenylphosphine (1.164 g, 4.439 mmol), and water (0.08 ml) in THF was stirred under nitrogen at room temperature. After ˜144 h, the reaction mixture was diluted with EtOAc (50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient) to give the desired product as a light yellow oil (.0796 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ1.18-1.40 (m, 6H), 1.63-1.71 (m, 2H), 2.50 (t, J=6.4 Hz, 2H), 3.82 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 7.01-7.06 (m, 2H), 7.87-7.92 (m, 2H); IR (KBr) 3410 (broad), 2940, 1710, 1605, 1510, 1260 cm−1; mass spectrum[(+)ESI], m/z 252 (M+H)+.

Workup

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vac
  4. customdried
  5. customThe residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-177677bf5cbb4a2a8dd52ccdd3f0c629
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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