HCID 44551319, compound → HCID 44551320, compound

HRID 2200838Notes

Reaction equation

HRID 2200838 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 44551319HCID 44551319, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 44551320HCID 44551320, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of aldehyde 13 (200 mg, 0.77 mmol) in THF (10 mL) at −78° C. was added slowly a solution of PhMgBr (2.7 mL, a 1.0 M solution in THF, 2.7 mmol). After the reaction mixture was stirred at this temperature for 30 min, the reaction was quenched with 1 M HCl (15 mL). The product was extracted with Et2O (2×20 mL). The organic layer was dried (Na2SO4), and concentrated, and the residue was purified by flash chromatography (hexane/EtOAc 3:1) to afford 14 (240 mg, 92%): Rf0.32 (hexane/EtOAc 3:1); 1H NMR (CDCl3) δ 2.96 (br s, 1H), 3.96 (s, 3H), 6.52 (s, 1H), 7.27 (m, 5H), 7.37 (s, 1H), 8.28 (s, 1H); 13C NMR (CDCl3) δ 57.0, 71.7, 110.5, 110.9, 127.1, 128.3, 128.7, 130.6, 140.6, 141.2, 160.0: ESI -HRMS [M+HCO2]− C15H1379BrNO6 calcd for m/z 381.9926, found 381.9931.

Workup

  1. customthe reaction was quenched with 1 M HCl (15 mL)
  2. extractionThe product was extracted with Et2O (2×20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-76f90b63b589462a84be33276ed7b9a6
Source dataset
uspto-grants-2016_06
Patent number
US09359389B2

Reaction notes

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