Triphenylphosphine → HCID 58629802, compound

HRID 1391770Notes

Reaction equation

HRID 1391770 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][CH2:39][O: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][CH2:39][O:40][CH3:41])[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 58629904HCID 58629904, compound

Product 1

HCID 58629802HCID 58629802, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diisopropylazodicarboxylate (1.44 mL, 7.31 mmol) in dry THF (50 mL) was added drop-wise, under nitrogen, over 1.5 h (using a syringe pump) to a solution ethyl (4-hydroxy-2-methylphenoxy)acetate (1.10 g, 5.21 mmol), 1-(6-bromo-2-pyridinyl)-3-(methyloxy)-1-propanol (1.29 g, 5.24 mmol) and triphenylphosphine (1.92 g, 7.32 mmol) in dry THF (50 mL) at 0° C. The resulting mixture was stirred under nitrogen and gradually allowed to warm to room temperature over 19 h. The solvent was then removed in vacuo and the residue purified by Biotage (silica, 90 g cartridge), eluting with cyclohexane:EtOAc 85:15 to afford the title compound as a pale yellow oil (1.32 g).

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified by Biotage (silica, 90 g cartridge)
  3. washeluting with cyclohexane:EtOAc 85:15

Sources & evidence

ORD record
ord-b1af7635fbba423dbd8919dc24b4748f
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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