Triphenylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]oxy}-2-methylphenyl)oxy]acetate

HRID 1391773Notes

Reaction equation

HRID 1391773 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=1.[Br:30][C:31]1[N:36]=[C:35]([CH:37](O)[CH2:38][O:39][CH2:40][CH3:41])[CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:30][C:31]1[N:36]=[C:35]([CH:37]([O:15][C:16]2[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=2)[CH2:38][O:39][CH2:40][CH3:41])[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 586298281-(6-Bromo-2-pyridinyl)-2-(ethyloxy)ethanol

Product 1

HCID 58629848Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]oxy}-2-methylphenyl)oxy]acetateYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisopropylazodicarboxylate (0.96 mL, 4.89 mmol) in dry THF (35 mL) was added drop-wise, under nitrogen, over 2 h (using a syringe pump) to a solution of ethyl (4-hydroxy-2-methylphenoxy)acetate (735 mg, 3.50 mmol), 1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (860 mg, 3.49 mmol) and triphenylphosphine (1.28 g, 4.88 mmol) in dry THF (35 mL) at 0° C. The resulting mixture was stirred under nitrogen and gradually allowed to warm to room temperature over 21 h. The solvent was then removed in vacuo and the residue purified by SPE (silica, 2×50 g cartridge), eluting with cyclohexane:EtOAc (gradient 20:1 to 1:1) to afford the title compound as an oil (966 mg).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified by SPE (silica, 2×50 g cartridge)
  3. washeluting with cyclohexane

Sources & evidence

ORD record
ord-d4c7e9cc36454a4bb05d83544fff421b
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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