Hydrochloric Acid → 1-Phenyl-3-buten-2-one

HRID 2294951Notes

Reaction equation

HRID 2294951 reaction equation
[CH:1]([Mg]Br)=[CH2:2].CON(C)[C:8](=[O:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O1CCCC1>[C:10]1([CH2:9][C:8](=[O:16])[CH:1]=[CH2:2])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10419762N-Methoxy-N-methyl-2-phenylacetamideHCID 178418507HCID 178418507, compound

Product 1

HCID 377341-Phenyl-3-buten-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of vinylmagnesium bromide in THF (80 mL, 80 mmol) was added dropwise to a stirred solution of N-methoxy-N-methylphenylacetamide (12.8 g, 71.5 mmol) in distilled tetrahydrofuran (THF) (200 mL), cooled to 0°-5° C. in an ice-water bath. The solution was stirred at 0°-5° C. for 2 h and was then poured into cold 1N HCl solution (150 mL). The THF layer was separated and the aqueous (aq.) layer was extracted with EtOAc (100 mL). Organic extracts were combined, dried (MgSO4), filtered and concentrated. The crude oil was chromatographed on a silica gel column and eluted with 5-20% ethylacetate (EtOAc) in hexanes to obtain title 4-phenyl-but-1-ene-3-one (7.62 g, 73%) as an oil.

Workup

  1. temperaturecooled to 0°-5° C. in an ice-water bath
  2. customThe THF layer was separated
  3. extractionthe aqueous (aq.) layer was extracted with EtOAc (100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude oil was chromatographed on a silica gel column
  8. washeluted with 5-20% ethylacetate (EtOAc) in hexanes

Sources & evidence

ORD record
ord-fe12891b8b7a4109899edadd3de55e0a
Source dataset
uspto-grants-1997_11
Patent number
US05691356

Reaction notes

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