Methyl vinyl ketone → HCID 19065568, compound

HRID 482147Notes

Reaction equation

HRID 482147 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=[O:11])=[CH:4][CH:3]=1.[CH:17]([C:19]([CH3:21])=[O:20])=[CH2:18].C(N(CC)CC)C>C(O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:10](=[O:11])[CH2:18][CH2:17][C:19](=[O:20])[CH3:21])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-

Product 1

HCID 19065568HCID 19065568, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(4-fluorophenoxy)benzaldehyde (26.8 g; 0.124M) in ethanol (60 ml) was added methyl vinyl ketone (8.32 ml; 0.1M), 3-benzyl-5-(2-hydroxyethyl)-4-methylthizolium chloride (5.93 g; 0.022M), and triethylamine (27.88 ml; 0.2M) at room temperature. After stirring for 6 hrs, volatiles were removed. To the residue was added water (200 ml), and the whole was extracted with ethyl acetate (150 ml×2). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residual oil was purified by flash column (SiO2) eluting with ethyl acetate-n-hexane (1:5) to give 19.03 g (yield 66.5%) of the subtitle compound [C] as a pale yellow oil.

Workup

  1. customvolatiles were removed
  2. additionTo the residue was added water (200 ml)
  3. extractionthe whole was extracted with ethyl acetate (150 ml×2)
  4. washThe combined organic layers were washed with water (100 ml), brine (100 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was purified by flash column (SiO2)
  8. washeluting with ethyl acetate-n-hexane (1:5)

Sources & evidence

ORD record
ord-25abd76cb43c4d528b9ae36e31a3727c
Source dataset
uspto-grants-1998_08
Patent number
US05792882

Reaction notes

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