Tetrahydrofuran → Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

HRID 369155Notes

Reaction equation

HRID 369155 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]1COCC1.C[Mg]I.[NH4+].[Cl-]>CCOCC>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:19]=[CH:18][C:10]([C:11]([OH:12])([CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 80389Ethyl 4-phenylbenzoylformateHCID 178418373HCID 178418373, compound

Product 1

HCID 21184093Ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-25 °C

Procedure

To a flame dried 500 mL flask flushed with N2, was added 24 g (100 mmol) of ethyl 4-phenylbenzoylformate and 300 mL of anhydrous THF. The solution was cooled with stirring to -25° C. and 37 mL (110 mmol) of a 3.0M solution of methylmagnesium iodide was added at a rate to maintain the reaction temperature below -10° C. The reaction progress was monitored by TLC and upon disappearance of starting material, 100 mL of saturated NH4Cl solution and 200 mL of ether were added. The organic layer was separated and washed with 2×50 mL of brine, dried (MgSO4) and concentrated leaving racemic ethyl 2-[(1,1'-biphenyl)-4-yl]-2-hydroxypropionate as an oil.

Workup

  1. customTo a flame dried 500 mL flask
  2. customflushed with N2
  3. temperatureThe solution was cooled
  4. temperatureto maintain the reaction temperature below -10° C
  5. additionwere added
  6. customThe organic layer was separated
  7. washwashed with 2×50 mL of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-50be1be0ae934e3d867263f82916f4a6
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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