Pyridine → Trifluoro-methanesulfonic acid 2-(3-benzyloxy-propoxy)-6-formyl-3-methyl-phenyl ester

HRID 2368006Notes

Reaction equation

HRID 2368006 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([OH:22])=[C:15]([CH:18]=[CH:19][C:20]=1[CH3:21])[CH:16]=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:30])([F:29])[S:25](O)(=[O:27])=[O:26].N1C=CC=CC=1>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:20]([CH3:21])=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=1[O:22][S:25]([C:24]([F:30])([F:29])[F:23])(=[O:27])=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 866647413-(3-Benzyloxy-propoxy)-2-hydroxy-4-methyl-benzaldehyde

Product 1

HCID 86664742Trifluoro-methanesulfonic acid 2-(3-benzyloxy-propoxy)-6-formyl-3-methyl-phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized according to the methods of general procedure 6 in U.S. Pat. Pub. No. 20090227541 (U.S. patent application Ser. No. 12/142,692) using the following reactants and amounts: 3-(3-Benzyloxy-propoxy)-2-hydroxy-4-methyl-benzaldehyde (0.3 g, 1.0 mmol), trifluoromethanesulfonic acid (0.34 mL, 2.0 mmol), pyridine (0.25 mL, 3.1 mmol), dichloromethane (15 mL). Purification: flash column chromatography (10-15% EtOAc/hexane): yield 0.25 g (59%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.14 (s, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.42-7.29 (m, 6H), 4.53 (s, 2H), 4.07 (t, J=6.4 Hz, 2H), 3.71 (t, J=6.1 Hz, 2H), 2.40 (s, 3H), 2.07-2.22 (m, 2H). 19F NMR (400 MHz, CDCl3) δ (ppm): −73.63 (s).

Workup

  1. customSynthesized
  2. customPurification

Sources & evidence

ORD record
ord-e4201be1e3bb42a3b14f7f7d48cefd76
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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