Benzyl Alcohol → Ethyl 1-benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

HRID 623736Notes

Reaction equation

HRID 623736 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[NH:10][C:9]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:41](O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:41]([N:10]1[C:11]([C:13]([F:15])([F:16])[F:14])=[CH:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:9]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86711826ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 86711825Ethyl 1-benzyl-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylateYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (2.0 g, 6.30 mmol) in dry THF (20 mL) was added triphenylphosphine (1.899 g, 7.24 mmol) and benzyl alcohol (0.720 mL, 6.92 mmol). DIAD (1.373 mL, 6.92 mmol) in dry THF (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for 1 h. THF was removed in vacuo. The crude product was dissolved in EtOAc (20 mL) and saturated NaHCO3 (40 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc (20 mL). The combined organic layer was washed with brine (50 mL) and dried over Na2SO4 and the solvent was evaporated. The residue was co-evaporated with DCM (10 mL) and then stirred in Et2O (20 mL) and the solids were filtered off. The filtrate was purified by column chromatography (silica, heptane/EtOAc, 3:1) to give 2.6 g (97%) the desired product as a yellow oil.

Workup

  1. customTHF was removed in vacuo
  2. dissolutionThe crude product was dissolved in EtOAc (20 mL)
  3. additionsaturated NaHCO3 (40 mL) was added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (20 mL)
  6. washThe combined organic layer was washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated
  9. stirringstirred in Et2O (20 mL)
  10. filtrationthe solids were filtered off
  11. customThe filtrate was purified by column chromatography (silica, heptane/EtOAc, 3:1)

Sources & evidence

ORD record
ord-9d6330ca43e34f99b7ec72ec54a531d3
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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