Sodium Hydroxide → HCID 14987382, compound

HRID 2082376Notes

Reaction equation

HRID 2082376 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-38c8e278aa0f4416a3359b4fbf80c379
Source dataset
uspto-grants-1993_02
Patent number
US05189048

Reaction notes

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