Water → HCID 178458843, compound

HRID 35771Notes

Reaction equation

HRID 35771 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([NH2:16])[C:9]=2[CH3:17])[CH2:5][C:4](=[O:18])[C:3]=1[C:19](=[O:22])[CH2:20][CH3:21].N1C=CC=CC=1.[C:29](Cl)(=[O:31])[CH3:30].O>ClCCl>[OH:18][C:4]1[CH2:5][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([NH:16][C:29](=[O:31])[CH3:30])[C:9]=2[CH3:17])[CH2:7][C:2](=[O:1])[C:3]=1[C:19](=[O:22])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 178458842HCID 178458842, compound

Product 1

HCID 178458843HCID 178458843, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (2.6 g; 8.6 mmole) and pyridine (0.7 g; 9 mmole) in dichloromethane (100 ml) was treated with acetyl chloride (0.69 g; 9 mmole) at 20° C. with stirring. After 1.5 hours the mixture was poured into water (100 ml) and shaken. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure using a rotary evaporator. The product was purified by chromatograpy over silica gel (eluent 1% methanol in dichloromethane) to give 3-hydroxy-5-(3-acetamido-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (1.0 g, 34%) as a pale orange semi-crystalline solid. Proton magnetic resonance spectrum (CDCl3, δ in ppm): 1.20 (3H, t); 2.18 (3H, s); 2.20 (3H, s); 2.27 (3H, s); 2.35 (3H, s); 2.4-4.0 (7H, m) 6.6 (1H, bs); 6.88 (1H, s); 18.20 (1H, s).

Workup

  1. stirringshaken
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customa rotary evaporator
  6. customThe product was purified by chromatograpy over silica gel (eluent 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b214bad77b7543e38487315bcc5effd3
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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