HCID 58497067, compound → HCID 57658727, compound

HRID 910047Notes

Reaction equation

HRID 910047 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]([OH:21])[C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[C:14](=[O:21])[C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH3:2]

Participants

4

Reactant 1

HCID 58497067HCID 58497067, compound

Product 1

HCID 57658727HCID 57658727, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-bromo-2-(1-hydroxy-3-trimethylsilanylprop-2-ynyl)phenoxy]acetic acid ethyl ester (0.95 g, 2.46 mmol) in CH2Cl2 (10 mL) was added activated MnO2 in 2 portions (1.5 g+1 g), and the reaction was stirred for 90 min. The solid was filtered off through a celite pad and the filtrate was concentrated in vacuo to give the title compound as yellow oil (0.83 g, 2.16 mmol, 87%). LC/MS (an 10p8) Rt 4.70 min, m/z 383 [M+H]+; 1H NMR (CDCl3): δ 0.30 (s, 9H), 1.30 (t, 3H), 4.27 (q, 2H), 4.72 (s, 2H), 6.81 (d, 1H), 7.58 (dd, 1H), 8.10 (s, 1H).

Workup

  1. filtrationThe solid was filtered off through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e48d574fc6fe4417b5cc6cd1796a8c40
Source dataset
uspto-grants-2011_09
Patent number
US08022063B2

Reaction notes

Loading…