Tetrahydrofuran → HCID 178450330, compound

HRID 2309139Notes

Reaction equation

HRID 2309139 reaction equation
[C:1]([CH:6]1[C:11](=[O:12])[CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-])=O)[CH:14]=2)[CH2:8][C:7]1=[O:24])(=[O:5])[CH2:2][CH2:3][CH3:4].[O:25]1CC[CH2:27][CH2:26]1>[Pd].[C]>[C:26]([NH:21][C:15]1[CH:14]=[C:13]([CH:9]2[CH2:10][C:11](=[O:12])[C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[C:7]([OH:24])[CH2:8]2)[CH:18]=[CH:17][C:16]=1[O:19][CH3:20])(=[O:25])[CH3:27]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 13644836HCID 13644836, compound

Product 1

HCID 178450330HCID 178450330, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

5.3 g of 2-butyryl-5-(3-nitro-4-methoxyphenyl)cyclohexane-1,3-dione in 300 ml of tetrahydrofuran were hydrogenated in the presence of 3 g of Pd/carbon (10%) under atmospheric pressure at 25° C. After 0.9 l of hydrogen had been absorbed, the mixture was dried over sodium sulfate and filtered, 1.3 g of sodium bicarbonate were added and the mixture was reacted with 1.2 g of acetyl chloride. After the mixture had been stirred for 16 hours, it was filtered and evaporated down. The remaining oil was brought to crystallization with diethyl ether, and the crystals were filtered off under suction. 3 g (55% yield) of 5-(3-acetylamino-4-methoxyphenyl)-2-butyryl-3-hydroxycyclohex-2-en-1-one of melting point 102°-106° C. were obtained.

Workup

  1. customAfter 0.9 l of hydrogen had been absorbed
  2. dry with materialthe mixture was dried over sodium sulfate
  3. filtrationfiltered
  4. addition1.3 g of sodium bicarbonate were added
  5. customthe mixture was reacted with 1.2 g of acetyl chloride
  6. filtrationit was filtered
  7. customevaporated down
  8. customThe remaining oil was brought to crystallization with diethyl ether
  9. filtrationthe crystals were filtered off under suction

Sources & evidence

ORD record
ord-61265b4dd93e44aa863e934d76b8b3f5
Source dataset
uspto-grants-1987_09
Patent number
US04692553

Reaction notes

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