Triphenylphosphine → HCID 58824154, compound

HRID 2266826Notes

Reaction equation

HRID 2266826 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][OH:11])[CH:9]=1)=[O:4].[I:13][C:14]1[CH:15]=[C:16](O)[CH:17]=[CH:18][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][O:11][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([I:13])[CH:19]=2)[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 122723-IodophenolHCID 5363146Diisopropyl azodicarboxylateHCID 58824163Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate

Product 1

HCID 58824154HCID 58824154, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1.85 g, 10.9 mmoles), 3-iodophenol (3.6 g, 16.35 mmoles), triphenylphosphine (4.3 g, 16.35 mmoles) in tetrahydrofuran (15 mL) was cooled to 0° C. Diisopropylazodicarboxylate (3.3 g, 16.35 mmoles) was added and the mixture was allowed to warm to room temperature, then stirred for 72 h. The tetrahydrofuran was evaporated and the residue purified by flash chromatography using hexane/ethyl acetate 7:3 v/v as eluent to give compound 106 (2.8 g). This was used directly in step (b).

Workup

  1. temperatureto warm to room temperature
  2. customThe tetrahydrofuran was evaporated
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-9a578529001646f69be120bb92723909
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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