Triphenylphosphine → HCID 18787403, compound

HRID 342080Notes

Reaction equation

HRID 342080 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](O)[C:7]=1[CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:17]1[C:8]2=[CH:9][CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18787383HCID 18787383, compound

Product 1

HCID 18787403HCID 18787403, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-[2-ethoxycarbonyl-6-hydroxyphenyl]butan-1-ol (5.14 g, 21.6 mmol) in THF (20 ml) was added dropwise to an ice bath cooled solution of triphenyl phosphine (7.37 g, 28.1 mmol) and diethyl azodicarboxylate (4.89 g, 28.1 mmol) in THF (60 ml). The reaction was stirred for 18 hr and then concentrated in vacuo. The residue was purified by chromatography on silica gel using methylene chloride as the eluent to give the product as an oil (2.85 g, 60%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-92077d1dcd054867acb826257bd1bfe6
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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