Diethylamine → HCID 9839040, compound

HRID 647908Notes

Reaction equation

HRID 647908 reaction equation
[CH:1]([C:3]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:2].[CH2:18]([N:20](CC)[CH2:21][CH3:22])[CH3:19].ClC(OCC)=O.C(NCC)C>ClCCl.CCOCC.O>[CH2:18]([N:20]([CH2:21][CH3:22])[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:4]1[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:3]=1[CH:1]=[O:2])[CH3:19]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 721625-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

Product 1

HCID 9839040HCID 9839040, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid (595 mg, 2.5 mM) was dissolved in dry dichloromethane (7.5 ml) under nitrogen with stirring and immersed in a cooling bath kept at -10° C. To this solution was added dropwise from a syringe triethylamine (0.35 ml, 2.5 mM). After 5 minutes was then similarly added ethyl chloroformate (0.25 ml, 2.5 mM). After 15 minutes was then similarly added diethylamine (0.26 ml, 2.5 mM). The reaction mixture was stirred at -10° C. (10 minutes) and then allowed to warm to 10°-15° C. After diluting with ether (50 ml) and water the aqueous layer was removed and the organic phase washed with dilute sodium bicarbonate solution and then quickly extracted with 2 N sodium hydroxide solution (1×25 ml). The layers were separated and the aqueous phase immediately acidified with dilute hydrochloric acid and extracted with ether/ethyl acetate. The combined extracts were washed with dilute sodium bicarbonate solution, water, dried (sodium sulphate) and evaporated. The oily residue was chromatographed on a short column of kieselgel G (40 g) eluting with chloroform-methanol (95:5) to give N,N-diethyl 5-(2-formyl-3-hydroxyphenoxy)pentanamide as a colourless oil, homogeneous by chromatography (chloroform:methanol, 95:5; Rf 0.35) and having NMR, IR and UV spectra consistent with the assigned structure.

Workup

  1. customimmersed in a cooling bath
  2. customkept at -10° C
  3. waitAfter 15 minutes was
  4. stirringThe reaction mixture was stirred at -10° C. (10 minutes)
  5. temperatureto warm to 10°-15° C
  6. customwas removed
  7. washthe organic phase washed with dilute sodium bicarbonate solution
  8. extractionquickly extracted with 2 N sodium hydroxide solution (1×25 ml)
  9. customThe layers were separated
  10. extractionextracted with ether/ethyl acetate
  11. washThe combined extracts were washed with dilute sodium bicarbonate solution, water
  12. dry with materialdried (sodium sulphate)
  13. customevaporated
  14. customThe oily residue was chromatographed on a short column of kieselgel G (40 g)
  15. washeluting with chloroform-methanol (95:5)

Sources & evidence

ORD record
ord-68782fa6370547a39dbd628076bfe741
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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