Pyridine → 2-(3-Benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl ester

HRID 426339Notes

Reaction equation

HRID 426339 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18](=[O:39])[CH:19]([C:24]1[CH:29]=[C:28](O)[CH:27]=[C:26]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=1)[CH2:20][C:21]([CH3:23])=[CH2:22].N1C=CC=CC=1>C(Cl)Cl>[CH3:16][O:17][C:18](=[O:39])[CH:19]([C:24]1[CH:29]=[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:27]=[C:26]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:25]=1)[CH2:20][C:21]([CH3:23])=[CH2:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 577549962-(3-Benzyloxy-5-hydroxyphenyl)-4-methyl-pent-4-enoic acid methyl ester

Product 1

HCID 577550372-(3-Benzyloxy-5-trifluoromethanesulfonyloxy-phenyl)-4-methyl-pent-4-enoic acid methyl esterYield 131.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (3.3 mL, 10.1 mmol) was added dropwise to a stirred solution of 2-(3-benzyloxy-5-hydroxyphenyl)-4-methyl-pent-4-enoic acid methyl ester (4.5 g, 13.8 mmol) and pyridine (3.0 mL, 38.7 mmol) in DCM (80 mL) at 0° C. then warmed to room temperature. After 1 h, the mixture washed with 1M HCl (50 mL), dried (MgSO4) and concentrated in vacuo to afford the title product as an orange oil (6.10 g, 96%). 1H-NMR (400 MHz, CDCl3): δ 7.42-7.30 (m, 5H), 6.97 (s, 1H), 6.85 (s, 1H), 6.78 (s, 1H), 5.05 (s, 3H), 4.75 (s, 1H), 4.64 (s, 1H), 3.77 (t, 1H), 3.66 (s, 3H), 2.77 (dd, 1H), 2.40 (dd, 1H), 1.69 (s, 3H).

Workup

  1. washthe mixture washed with 1M HCl (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-edd83f0a0ab74075b2719ab86dc0e749
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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