3-Furanol, tetrahydro- → Methyl 4'-methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylate

HRID 1845313Notes

Reaction equation

HRID 1845313 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:39]1[CH2:43][CH2:42][O:41][CH2:40]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][CH:39]3[CH2:43][CH2:42][O:41][CH2:40]3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 58188199Methyl 4'-methyl-5-(tetrahydrofuran-3-yloxy)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (120 mg, 0.47 mmol), triphenylphosphine (120 mg, 0.47 mmol), 3-hydroxytetrahydrofuran (45 mg, 0.50 mmol) in CH2Cl2 (7 mL) at rt was slowly added a solution of diisopropyl azodicarboxylate (100 mg, 0.50 mmol) in CH2Cl2 (2 mL). The mixture was stirred at rt overnight, and then concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3c061264a35c4d57a36ee264091fd7bb
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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