Triphenylphosphine → HCID 58629900, compound

HRID 1391802Notes

Reaction equation

HRID 1391802 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=1.[CH2:16]([O:18][CH2:19][C@@H:20]([C:22]1[N:27]=[C:26]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[CH:25]=[CH:24][CH:23]=1)O)[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([C:26]2[N:27]=[C:22]([C@H:20]([O:1][C:2]3[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([CH3:15])[CH:3]=3)[CH2:19][O:18][CH2:16][CH3:17])[CH:23]=[CH:24][CH:25]=2)=[CH:29][CH:30]=1)#[N:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 58629869HCID 58629869, compound

Product 1

HCID 58629900HCID 58629900, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of ethyl [(4-hydroxy-2-methylphenyl)oxy]acetate (664 mg, 3.16 mmol), 4-{6-[(1R)-2-(ethyloxy)-1-hydroxyethyl]-2-pyridinyl}benzonitrile (719 mg, 2.68 mmol) and triphenylphosphine (857 mg, 3.27 mmol) in dry DCM (35 mL) was cooled to 0° C. under nitrogen. DIAD (633 μL, 3.21 mmol) was added dropwise over 10 min, and the reaction mixture stirred at 0° C. for a further 2 h. DCM (120 mL) was added to the reaction mixture, washed with aq 1M NaOH (50 mL) and water (100 mL), dried (Na2SO4) and evaporated to give a yellow oil. Purification by Biotage™ chromatography (silica, 90 g cartridge) eluting with cyclohexane:EtOAc (8:1) afforded the title compound as a colourless oil (765 mg).

Workup

  1. washwashed with aq 1M NaOH (50 mL) and water (100 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto give a yellow oil
  5. customPurification by Biotage™ chromatography (silica, 90 g cartridge)
  6. washeluting with cyclohexane:EtOAc (8:1)

Sources & evidence

ORD record
ord-c9e8b855c685469893a2cded33eadedf
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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