Triphenylphosphine → HCID 67076643, compound

HRID 521447Notes

Reaction equation

HRID 521447 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-32b6a4dce9924300a279cd0b3f6bdc19
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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