Triphenylphosphine → HCID 67076643, compound

HRID 2094674Notes

Reaction equation

HRID 2094674 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:33][C:34]1[CH:35]=[C:36]([CH2:40][CH2:41]O)[CH:37]=[CH:38][CH:39]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:2]([O:1][CH2:41][CH2:40][C:36]2[CH:37]=[CH:38][CH:39]=[C:34]([Br:33])[CH:35]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27340902-(3-Bromophenyl)ethan-1-olHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67076643HCID 67076643, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-hydroxy-4-methoxybenzoate (500 mg, 2.75 mmol) and triphenylphosphine (1.08 g, 4.12 mmol) were dissolved in THF (13 ml), the solution was cooled in an ice bath and 2-(3-bromophenyl)-ethanol (662 mg, 3.29 mmol) and DIAD (886 mg, 4.12 mmol) were added sequentially. Stirring was continued for 3 h at room temperature. The reaction mixture was evaporated to dryness and the residue purified by preparative RP HPLC (water/ACN gradient) to give 900 mg of the title compound.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-8fdbb54bfdc14d289b1018024d023b95
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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