Triphenylphosphine → 2-[(5-Hexynyl)oxy]benzenepropanoic acid methyl ester

HRID 1648035Notes

Reaction equation

HRID 1648035 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:6][CH2:5][CH2:4][CH2:3][C:2]#[CH:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 702345-Hexyn-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2794569Methyl 3-(2-hydroxyphenyl)propionate

Product 1

HCID 537894482-[(5-Hexynyl)oxy]benzenepropanoic acid methyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.98 g (10 mmol) of 5-hexyn-1-ol, 1.98 g (11 mmol) of 2-hydroxybenzenepropanoic acid methyl ester, 2.88 g (11 mmol) of triphenylphosphine, 1.91 g (11 mmol) of diethyl azodicarboxylate, and 220 mL of dry tetrahydrofuran was stirred at room temperature for 100 hr and then concentrated under reduced pressure. The residue was triturated with 9:1 hexane-ether. The solid was filtered with suction and washed with the same solvent mixture. The filtrate and washes were combined and concentrated in vacuo. Flash chromatography of the residue on silica gel, eluting with 9:1 hexane-ether gave 2 g (77%) of 2-[(5-hexynyl)oxy]benzenepropanoic acid methyl ester as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with 9:1 hexane-ether
  3. filtrationThe solid was filtered with suction
  4. washwashed with the same solvent mixture
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography of the residue on silica gel, eluting with 9:1 hexane-ether

Sources & evidence

ORD record
ord-ca4921c997bc4acaa14a72107dae2424
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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