Dimethylformamide → (RS)-2-biphenyl-4-yl-2-ethoxy-propionic acid ethyl ester

HRID 1247333Notes

Reaction equation

HRID 1247333 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[H-].[Na+].[CH2:21](I)[CH3:22].CN(C=O)C.[CH2:29]1COC[CH2:30]1>O>[CH2:29]([O:9][C:8](=[O:10])[C:7]([C:4]1[CH:5]=[CH:6][C:1]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:2][CH:3]=1)([O:12][CH2:21][CH3:22])[CH3:11])[CH3:30]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 6340Iodoethane3×HCID 8028TetrahydrofuranHCID 24758Sodium hydride3×HCID 33670892-(1,1'-Biphenyl)-4-YL-2-hydroxypropanoic acid

Product 1

HCID 69288732(RS)-2-biphenyl-4-yl-2-ethoxy-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-biphenyl-4-yl-2-hydroxy-propionic acid (CAS-6244-54-8, 943 mg) in THF (10 ml), stirred at 0° C. was added NaH (60% in mineral oil, 342 mg). After 50 min, ethyl iodide (0.69 ml) was added and the mixture was stirred at rt for 14 h. DMF (10 ml) was added. After 2 days, 47 mg NaH and 0.16 ml ethyl iodide were added subsequently. In the course of three weeks, a total of 653 mg NaH and 1.32 ml ethyl iodide were added. Water was added and the mixture was extracted with EtOAc (2×). The organic phase was washed with water, dried, filtered and evaporated. The crude product was purified by flash chromatography (EtOAc/cyclohexane 5:95=>1:4) to give (RS)-2-biphenyl-4-yl-2-ethoxy-propionic acid ethyl ester (276 mg) as a light yellow oil. MS 298.1 ([M]+)

Workup

  1. waitAfter 2 days
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe organic phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography (EtOAc/cyclohexane 5:95=>1:4)

Sources & evidence

ORD record
ord-c4487bfebec44958b95a844d6f16034d
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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