Acetic Acid → 4-(2-Carboxy-2-ethoxy-ethyl)-benzoic acid 4-methanesulfonyloxy-benzyl ester

HRID 709505Notes

Reaction equation

HRID 709505 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:34]=[CH:33][C:9]([CH2:10][O:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([O:29][CH2:30][CH3:31])[C:21]([O:23]CC(Cl)(Cl)Cl)=[O:22])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C(O)(=O)C>C(Cl)Cl.[Zn]>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12](=[O:32])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([C:21]([OH:23])=[O:22])[O:29][CH2:30][CH3:31])=[CH:15][CH:14]=2)=[CH:33][CH:34]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 866503074-[2-Ethoxy-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methane sulfonyloxy-benzyl ester

Product 1

HCID 866503144-(2-Carboxy-2-ethoxy-ethyl)-benzoic acid 4-methanesulfonyloxy-benzyl ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-ethoxy-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methane sulfonyloxy-benzyl ester (0.02 g, 0.036 mmol) in dry DCM (2 mL) was first added zinc dust (0.047 g, 0.722 mmol), then acetic acid (1.08 mL, 18.06 mmol) at 0° C. The resulting inhomogeneous mixture was stirred for 17 h without removing the ice bath. The zinc was filtered off and washed with DCM and MeOH and the remaining filtrates were combined and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM/MeOH (92:8) as the eluent. The title compound was obtained as an oil (0.005 g, 36%). 1H NMR (400 MHz, CDCl3): δ 7.91-7.93 (d, 2H), 7.42-7.44 (d, 2H, 7.19-7.24 (m, 4H), 5.27 (s, 2H), 4.03 (m, 1H), 3.52 (m, 1H), 3.37 (m, 1H), 2.99-3.14 (m, 2H), 3.08 (s, 3H), 2.63 (t, 3H). Mass Spectrum: M−H+ 421.23.

Workup

  1. customat 0° C
  2. customwithout removing the ice bath
  3. filtrationThe zinc was filtered off
  4. washwashed with DCM and MeOH
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-fbf367028dd74c4283ba7e65995d5157
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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