Sodium Hydroxide → HCID 178458838, compound

HRID 2291235Notes

Reaction equation

HRID 2291235 reaction equation
[OH-:1].[Na+].[OH:3][C:4]1[CH2:9][CH:8]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([CH2:18][C:19]#[N:20])[C:11]=2[CH3:21])[CH2:7][C:6](=[O:22])[C:5]=1[C:23](=[O:26])[CH2:24][CH3:25]>C1(C)C=CC=CC=1>[OH:3][C:4]1[CH2:9][CH:8]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([CH2:18][C:19](=[O:1])[NH2:20])[C:11]=2[CH3:21])[CH2:7][C:6](=[O:22])[C:5]=1[C:23](=[O:26])[CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178458837HCID 178458837, compound

Product 1

HCID 178458838HCID 178458838, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium hydroxide solution (10%, 4 ml) was added to a solution of 3-hydroxy-2-propionyl-5-(3-cyanomethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.5 g, 4.6 mmol) in toluene (10 ml) and the mixture was refluxed for 2 h. After cooling the toluene was separated and the aqueous layer acidified and extracted with ethylacetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. Chromatography on silica gel (elution with an increasing gradient of ethylacetate in methylene chloride) gave 3-hydroxy-2-propionyl-5-(3-carbamoylmethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a pale solid (0.6 g, 40%). Proton magnetic resonance spectrum (CDCl3 ; 67 in ppm): 1.25 (3H,t,J6.5 Hz); 2.24 (3H,s); 2.28 (3H,s); 2.32 (3H,s); 2.2-4.2 (7H,m); 3.60 (2H,s); 5.3 (1H,brs); 6.0 (1H,brs); 6.85 (1H,s); 18.10 (1H,s). Infrared spectrum (CHCl3): ν max 1670 b cm-1. Also recovered from the chromatography was a sodium bicarbonate soluble fraction identified as 2-[3-(4-propionyl-5-hydroxycyclohex-3-one-4-enyl)-2,4,6-trimethylpheny]acetic acid (0.25 g, 17%) a colourless solid. Proton magnetic resonance spectrum (CDCl3 ; δ in ppm): 1.2 (3H, t,J6.5 Hz); 2.13 (3H,s); 2.2 (3H,s); 2.26 (3H, s); 2.3-4.1 (7H,m); 3.50; (2H,s); 6.75 (1H,s). Infrared spectrum: ν max (NUjol) 3300-2500 b, 1680-1630 b cm-1.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customwas separated
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washChromatography on silica gel (elution with an increasing gradient of ethylacetate in methylene chloride)

Sources & evidence

ORD record
ord-dbf4ff65e3b94e59a8166501a17507a3
Source dataset
uspto-grants-1989_01
Patent number
US04795487

Reaction notes

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