4-Hydroxybiphenyl → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 2266788Notes

Reaction equation

HRID 2266788 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].O[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([CH3:12])=[C:8]([CH2:10][O:11][C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=3)=[CH:21][CH:22]=2)[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 71034-Hydroxybiphenyl2×HCID 11776TriphenylphosphineHCID 58824163Methyl 4-(hydroxymethyl)-5-methylfuran-2-carboxylate

Product 1

HCID 588241734-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-hydroxymethyl-5-methyl-furan-2-carboxylic acid methyl ester (16) (1 g) in anhydrous tetrahydrofuran (20 mL) was cooled to 0° C. under a nitrogen atmosphere. 4-Hydroxybiphenyl (3 g) and triphenylphosphine (4.61 g) were added and the mixture was treated with di-isopropylazodicarboxylate (3.46 mL) dropwise. The mixture was stirred at 0° C. for 10 min then cooling was removed and the mixture stirred for a further 3 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (50 mL) and water (100 mL). The organic phase was separated, dried and evaporated. The residue was purified by flash chromatography, eluting with pentane/ethyl acetate 9:1 by volume to give a mixture of the title compound and 4-hydroxybiphenyl (1.8 g). This material was purified further by flash chromatography eluting with dichloromethane/methanol 99:1 by volume to give compound 17 as a white solid (200 mg). LCMS System A: Rt=4.2 mins.

Workup

  1. temperaturethen cooling
  2. customwas removed
  3. stirringthe mixture stirred for a further 3 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue was partitioned between ethyl acetate (50 mL) and water (100 mL)
  6. customThe organic phase was separated
  7. customdried
  8. customevaporated
  9. customThe residue was purified by flash chromatography
  10. washeluting with pentane/ethyl acetate 9:1 by volume
  11. customto give

Sources & evidence

ORD record
ord-b219eea6b2ea4525bae9d46bd8ec188c
Source dataset
uspto-grants-2010_12
Patent number
US07858644B2

Reaction notes

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