Chloroform → HCID 66846703, compound

HRID 254177Notes

Reaction equation

HRID 254177 reaction equation
[CH:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:17].C(Cl)(Cl)Cl>ClCCl>[CH:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-:17])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 22951086HCID 22951086, compound

Product 1

HCID 66846703HCID 66846703, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-isopropoxymethylpyridine (18.4 g, 0.121 mol) in dichloromethane (200 mL) at room temperature was treated portionwise with meta-chloroperoxybenzoic acid (42.1 g, 0.121 mol), stirred for 3 h, poured into CHCl3 (450 mL) and washed with 2.5-M aqueous NaOH solution (2×250 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound as a pale yellow oil; NMR δH (400 MHz, CDCl3), 1.19-1.21 (6H, d, J=6 Hz), 3.71-3.80 (1H, sept, J 6.5 Hz), 4.58 (2H, s), 7.37 (2H, m), 7.47-7.49 (1H, d, J 7 Hz) and 8.25-8.27 (1H, d, J 7.5 Hz)

Workup

  1. washwashed with 2.5-M aqueous NaOH solution (2×250 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39b29c0060ea41a2b67d4878b1e5e503
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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