Methyl vinyl ketone → HCID 10060908, compound

HRID 1735824Notes

Reaction equation

HRID 1735824 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]([C:12]([CH3:14])=[O:13])=[CH2:11]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(N(CC)CC)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4](=[O:5])[CH2:11][CH2:10][C:12](=[O:13])[CH3:14]

Participants

5

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 811292-Bromobenzaldehyde

Product 1

HCID 10060908HCID 10060908, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 90 g of bromobenzaldehyde, 41 g of methyl vinyl ketone, 24.2 g of 3-benzyl-4-methyl-5-hydroxyethylthiazolium chloride is added with 45 ml of triethylamine. A marked exothermicity is observed, at the end of which the reaction mixture is heated to 70° C. under stirring for 4 h. The resulting mixture is cooled and partitioned between 800 ml of ether and 400 ml of H2O. The aqueous phase is reextracted and the combined organic phases are washed with 10% HCl and with brine, then dried over Na2SO4 and the solvent is evaporated off. 110 g of an orange oil are obtained (93% yield). 1H NMR (CDCl3), δ: 2.22 (s, 3 H), 2.89 (t, 2 H), 3.15 (t, 2 H), 7.18-7.65 (m, 4 H).

Workup

  1. temperatureThe resulting mixture is cooled
  2. custompartitioned between 800 ml of ether and 400 ml of H2O
  3. washthe combined organic phases are washed with 10% HCl and with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off

Sources & evidence

ORD record
ord-7f8d1191aaf8448f9a5afec686a7c219
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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