Triphenylphosphine → HCID 59634051, compound

HRID 1615051Notes

Reaction equation

HRID 1615051 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[I:12][C:13]1[CH:18]=[CH:17][C:16](O)=[C:15]([O:20][CH3:21])[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH2:10][O:11][C:16]3[CH:17]=[CH:18][C:13]([I:12])=[CH:14][C:15]=3[O:20][CH3:21])=[CH:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 101061274-iodo-2-methoxyphenolHCID 22135711(4-Cyclopropylphenyl)methanol2×

Product 1

HCID 59634051HCID 59634051, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-cyclopropylphenyl)methanol (4.5 g) prepared in (2) and 4-iodo-2-methoxyphenol (7.5 g) in THF (40 mL) were added triphenylphosphine (8.7 g) and diisopropyl azodicarboxylate (6.5 mL) at 0° C. The reaction mixture was stirred at RT for 22 hr. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1) to give the title compound (5.3 g, 46%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-a476af6fbb1b46b9b5941c6d573f83ac
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

Loading…