Tetrahydrofurfuryl alcohol → Methyl 4'-methyl-5-((tetrahydrofuran-2-yl)methoxy)biphenyl-3-carboxylate

HRID 1845316Notes

Reaction equation

HRID 1845316 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:38]1[CH2:42][CH2:41][CH2:40][CH:39]1[CH2:43]O.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][CH2:43][CH:39]3[CH2:40][CH2:41][CH2:42][O:38]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 7360Tetrahydrofurfuryl alcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 58187973Methyl 4'-methyl-5-((tetrahydrofuran-2-yl)methoxy)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (150 mg, 0.59 mmol), triphenylphosphine (150 mg, 0.59 mmol), tetrahydro-2-furanmethanol (60 mg, 0.59 mmol) in CH2Cl2 (8 mL) at rt was slowly added a solution of diisopropyl azodicarboxylate (200 mg, 1.0 mmol) in CH2Cl2 (3 mL). The mixture was stirred at room temperature 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-09489a175fb842d98f020a1074b6f0d9
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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