Triethylamine → HCID 9816133, compound

HRID 647907Notes

Reaction equation

HRID 647907 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](O)=[O:11])=[O:2].C([N:20](CC)CC)C.ClC(OCC)=O.[Cl-].[NH4+]>O1CCCC1.O.CCOCC.C(OCC)(=O)C.Cl>[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]([NH2:20])=[O:11])=[O:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 721625-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

Product 1

HCID 9816133HCID 9816133, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 21584169Diethylether ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid (595 mg, 0.0025 M) was dissolved in dry tetrahydrofuran (5.5 ml) and immersed in a cooling bath kept at -10° C. To the stirred solution under nitrogen was added dropwise from a syringe triethylamine (0.35 ml, 0.0025 M). After 5 minutes was then similarly added ethyl chloroformate (0.25 ml, 0.0025 M). After 15 minutes was then added a solution of ammonium chloride (0.4 g) in water (1.1 ml) and tetrahydrofuran (1.6 ml) previously cooled to 0° C. The vigorously stirred mixture was allowed to come to room temperature over 30 minutes, stirred at room temperature (15 minutes), and then diluted with ether/ethyl acetate (1:1) and 1 N hydrochloric acid. The layers were separated and the organic layer washed with dilute sodium bicarbonate solution and then quickly extracted with 2 N sodium hydroxide (1×25 ml). The layers were separated and the aqueous phase immediately acidified with dilute hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with dilute sodium bicarbonate solution, water, dried (sodium sulphate) and evaporated to give 5-(2-formyl-3-hydroxyphenoxy)pentanamide, m.p. 94°-95° C. from ethyl acetate/petrol.

Workup

  1. customimmersed in a cooling bath
  2. customkept at -10° C
  3. waitto come to room temperature over 30 minutes
  4. customThe layers were separated
  5. washthe organic layer washed with dilute sodium bicarbonate solution
  6. extractionquickly extracted with 2 N sodium hydroxide (1×25 ml)
  7. customThe layers were separated
  8. extractionextracted with ethyl acetate
  9. washThe combined extracts were washed with dilute sodium bicarbonate solution, water
  10. dry with materialdried (sodium sulphate)
  11. customevaporated

Sources & evidence

ORD record
ord-96d26c1db23649c0b3095fca3bf1feaf
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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