Triphenylphosphine → HCID 53789448, compound

HRID 327987

Reaction equation

HRID 327987 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 53789448HCID 53789448, compoundYield 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-c4f18eed0fca40d3832b567c6507aed1
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Linked notes

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