m-Chloroperbenzoic acid → Tert-butyl{4-chloro-2-[(4-methyl-1-oxidopyridin-3-yl)ethynyl]phenoxy}acetate

HRID 2390129Notes

Reaction equation

HRID 2390129 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:19]=[N+:20]([O-:34])[CH:21]=[CH:22][C:23]=1[CH3:24])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58521948Tert-butyl{4-chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate2×

Product 1

HCID 58522001Tert-butyl{4-chloro-2-[(4-methyl-1-oxidopyridin-3-yl)ethynyl]phenoxy}acetateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl{4-chloro-2-[(4-methylpyridin-3-yl)ethynyl]phenoxy}acetate (Intermediate 19; 110 mg; 0.31 mmol) in DCM (5 mL) was treated with 3-chloroperbenzoic acid (91 mg; 0.37 mmol) and stirred at RT for 2 hours. The solvents were removed under vacuum, the residue was taken up in EtOAc and the organic phase washed with a saturated bicarbonate solution twice, then with brine. The organic layer was then dried over MgSO4 and concentrated under vacuum to afford the title compound (110 mg, 96%) as a white solid.

Workup

  1. customThe solvents were removed under vacuum
  2. washthe organic phase washed with a saturated bicarbonate solution twice
  3. dry with materialThe organic layer was then dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e7c1a8b36c04ee88be3fee0dba5038e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…