Tetrahydrofuran → HCID 21286525, compound

HRID 1906752Notes

Reaction equation

HRID 1906752 reaction equation
[CH2:1]([NH:4][C:5](=O)[CH2:6][O:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=1[Cl:16])[CH:2]=[CH2:3].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[Cl:14][C:13]1[CH:12]=[C:11]([Cl:15])[CH:10]=[C:9]([Cl:16])[C:8]=1[O:7][CH2:6][CH2:5][NH:4][CH2:1][CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21286507HCID 21286507, compound

Product 1

HCID 21286525HCID 21286525, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

N-allyl-2,4,6-trichlorophenoxyacetamide, 14.6 gm, was added to 100 ml of anhydrous tetrahydrofuran. The solution was cooled to about 10° C. with an ice bath. Then lithium aluminum hydride, 1.86 gm, was added slowly. The resulting mixture was stirred in the cold and allowed to warm to room temperature overnight. The mixture was heated at reflux for 6 hours, then again stirred at room temperature overnight. Then 2 ml water, 2 ml of 15% NaOH solution and 6 ml of water were added sequentially. The mixture was filtered through a pad of Celite and the filtrate stripped to yield 10.6 gm of N-allyl ethanolamine 2,4,6-trichlorophenylether as an oil.

Workup

  1. temperatureto warm to room temperature overnight
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 6 hours
  4. stirringagain stirred at room temperature overnight
  5. filtrationThe mixture was filtered through a pad of Celite

Sources & evidence

ORD record
ord-dd06979b6c9f4d5ebbfc04285dcf2041
Source dataset
uspto-grants-1987_03
Patent number
US04654346

Reaction notes

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