Dimethylamine → (2E)-4-(Dimethylamino)-2-butenoic acid

HRID 1246290Notes

Reaction equation

HRID 1246290 reaction equation
[CH3:1][NH:2][CH3:3].C[Si]([O:8][C:9](=[O:14])/[CH:10]=[CH:11]/[CH2:12]Br)(C)C>O1CCCC1>[CH3:1][N:2]([CH3:3])[CH2:12]/[CH:11]=[CH:10]/[C:9]([OH:8])=[O:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 12730183Trimethylsilyl-4-bromocrotonate

Product 1

HCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 211 ml of dimethylamine (2M in tetrahydrofuran, 0.422 moles) is added dropwise to a solution of 50 g trimethylsilyl-4-bromocrotonate (0.211 moles, 75.9% by GC-MS) in 250 ml of tetrahydrofuran at 0–5° C. under N2. The reaction mixture is stirred at room temperature for 30 minutes. A white solid by-product is removed by filtering and 2 ml water is added to the filtrate followed by seeding. The crystals formed are filtered and washed with ether to give 18.3 g (from two crops) of the desired product as off-white solid. Yield is 67.2% (98% purity by GC-MS, NMR is consistent with the expected structure).

Workup

  1. customA white solid by-product is removed
  2. filtrationby filtering
  3. addition2 ml water is added to the filtrate
  4. customThe crystals formed
  5. filtrationare filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-cf1b42643b424fdb96cf89c3f3c034f9
Source dataset
uspto-grants-2006_10
Patent number
US07126025B2

Reaction notes

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