Sodium Hydroxide → HCID 178458851, compound

HRID 2291234Notes

Reaction equation

HRID 2291234 reaction equation
[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[C:17]([CH3:18])=[C:16]([CH2:19][C:20]#[N:21])[C:15]([CH3:22])=[C:14]([C:23](=[O:25])[CH3:24])[C:13]=2[CH3:26])[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].[OH-:28].[Na+]>>[C:1]([C:5]1[C:6](=[O:27])[CH2:7][CH:8]([C:12]2[C:17]([CH3:18])=[C:16]([CH2:19][C:20](=[O:28])[NH2:21])[C:15]([CH3:22])=[C:14]([C:23](=[O:25])[CH3:24])[C:13]=2[CH3:26])[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 178458850HCID 178458850, compound

Product 1

HCID 178458851HCID 178458851, compoundYield 65%

Procedure

A solution of 2-propionyl-3-hydroxy-5-(3-acetyl-5-cyanomethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.67 g, 1.83 mmol) in 5% aqueous sodium hydroxide (12 ml) was refluxed for 30 min. The solution was then cooled, acidified and extracted with ethylacetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbon solution, further water then dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to yield 2-propionyl-3-hydroxy-5-(3-acetyl-5-carbamoylmethyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a colourless solid (0.49 g, 65%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm): 1.14 (3H,t); 2.13 (3H,s); 2.22 (3H,s); 2.32 (3H,s); 2.46 (3H,s); 2.4-3.9 (7H, m); 3.61 (2H,s); 5.48 (1H,brs); 6.10 (1H,brs); 18.00 (1H,brs). The sodium hydrogen carbonate solution washings were acidified and extracted with ethylacetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure to yield 2-[3-(4-propionyl-5-hydroxycyclohex-3-one-4- enyl)-5-acetyl-2,4,6-trimethylphenyl]acetic acid (0.11 g, 16%) as a colourless solid.

Workup

  1. temperatureThe solution was then cooled
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbon solution, further water
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-28607a68b0ca4b2188abe9204c74ee08
Source dataset
uspto-grants-1989_01
Patent number
US04795487

Reaction notes

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