Sodium Hydroxide → HCID 14987382, compound

HRID 2371460Notes

Reaction equation

HRID 2371460 reaction equation
[CH2:1]([C:4]1[NH:8][C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.[OH-].[Na+]>C(Cl)Cl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:1]([C:4]1[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:15][CH:14]=2)[C:7]([CH:9]=[O:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 14987392HCID 14987392, compound

Product 1

HCID 14987382HCID 14987382, compoundYield 132.4%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-n-propylpyrrole-2-carboxaldehyde (2.5 g, 18.9 mmol) and t-butyl 4'-bromomethylbiphenyl-2-carboxylate (7.2 g, 20.7 mmol) in methylene chloride (75 ml) was added 2.5N NaOH (15 ml) and Aliquat 336 (1.5 g, 3.7 mmol). The mixture was vigorously stirred at room temperature overnight (~18 hours). The organic phase was washed with water (50 ml) and saturated aqueous sodium chloride (50 ml) before being dried (MgSO4), filtered and concentrated to leave 10.1 g of a dark oily residue. Flash chromatography (silica gel, 300 g; EtOAc/hexanes, 1/9) gave 5.84 g (79%) of a pale yellow viscous oil.

Workup

  1. washThe organic phase was washed with water (50 ml) and saturated aqueous sodium chloride (50 ml)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-de5f4e078347437c96fb2c242e63f2a6
Source dataset
uspto-grants-1992_03
Patent number
US05093346

Reaction notes

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