Ammonia → HCID 21411766, compound

HRID 2071652Notes

Reaction equation

HRID 2071652 reaction equation
N.[K].[CH2:3]([O:5][CH:6]([O:15][CH2:16][CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[CH3:4].[CH2:18]1[O:20][CH2:19]1.[Cl-].[NH4+]>C(OCC)C>[CH2:16]([O:15][CH:6]([O:5][CH2:3][CH3:4])[CH2:7][CH:8]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[CH2:18][CH2:19][OH:20])[CH3:17]

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 6354Ethylene OxideHCID 25517Ammonium ChlorideHCID 5462222PotassiumHCID 21411769HCID 21411769, compound

Product 1

HCID 21411766HCID 21411766, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To stirred liquid ammonia (2 liters) was added ferric nitrate (0.1 gm) followed by potassium metal (14 gms) in 1 gram pieces over a period of 20 minutes. To the resulting solution 3-(4-pyridyl)-propionaldehyde diethyl acetal (21 gms) was added over a period of 3 minutes and a deep yellow colour was allowed to develop over a period of 2 hours. Liquid ethylene oxide (25 mls) was then added and the mixture was stirred for a further 3 hours. Solid ammonium chloride (20 gms) was added in small portions followed by diethyl ether (1 liter). The ammonia was allowed to evaporate overnight and the residual mixture was filtered. The solvent was evaporated from the filtrate and the residual oil was distilled to give 1,1-diethoxy-3-(4-pyridyl)-pentan-5-ol (18 gms, 70% conversion) b.p. 170°-175° C/1 mm Hg, as a thick colourless oil.

Workup

  1. customto evaporate overnight
  2. filtrationthe residual mixture was filtered
  3. customThe solvent was evaporated from the filtrate
  4. distillationthe residual oil was distilled

Sources & evidence

ORD record
ord-cb329e49a81741caac8dbf74f0f328e4
Source dataset
uspto-grants-1977_09
Patent number
US04048180

Reaction notes

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