Sodium hydride → 1,3-Diethyl 2-[2'-chloro-4'-(trifluoromethyl) [1,1'-biphenyl]-3-yl]propanedioate

HRID 628475Notes

Reaction equation

HRID 628475 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=1>C(=O)(OCC)OCC>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 66973842Ethyl 2'-chloro-4'-(trifluoromethyl)[1,1'-biphenyl]-3-acetate

Product 1

HCID 669736161,3-Diethyl 2-[2'-chloro-4'-(trifluoromethyl) [1,1'-biphenyl]-3-yl]propanedioate

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Procedure

NaH (1.2 g, 60% dispersion in mineral oil) was added to the product of Step A dissolved in diethyl carbonate (10 mL). The reaction mixture was stirred overnight and then cautiously quenched by careful addition to saturated aqueous ammonium chloride solution. The quenched reaction mixture was extracted with ethyl acetate, and the separated orgranic phase was dried and concentrated under vacuum to yield 2.1 g of the title compound containing approximately 30% diethyl carbonate. 1H NMR (CDCl3) δ 7.74 (s, 1H), 7.57 (d, 1H), 7.35-7.55 (m, 5H), 4.57 (s, 1H) 4.19 (q, 4H), 1.29 (t, 6H).

Workup

  1. customcautiously quenched by careful addition to saturated aqueous ammonium chloride solution
  2. customThe quenched reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. customthe separated orgranic phase was dried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-90074f2421644f42b679957fed90ad88
Source dataset
uspto-grants-2016_04
Patent number
US09314025B2

Reaction notes

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