Acetic Acid → (3-tert-Butyl-4-hydroxy-5-{[(2-hydroxyethyl)(methyl)amino]methyl}phenyl)(thiophen-2-yl)methanone

HRID 1651131Notes

Reaction equation

HRID 1651131 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=1)=[O:7].[CH3:19][NH:20][CH2:21][CH2:22][OH:23].C=O.[C:26](O)(=O)C>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[C:12]([CH2:19][N:20]([CH2:21][CH2:22][OH:23])[CH3:26])[C:11]([OH:14])=[C:10]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 80162-(Methylamino)ethanolHCID 14751214HCID 14751214, compound

Product 1

HCID 3079270(3-tert-Butyl-4-hydroxy-5-{[(2-hydroxyethyl)(methyl)amino]methyl}phenyl)(thiophen-2-yl)methanoneYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(1,1-Dimethylethyl)-4-hydroxyphenyl 2-thienyl ketone (22.0 g) was dissolved in 440 ml of ethanol and heated to reflux for 6 hours with 12.7 g of N-methylethanolamine, 14.5 g of a 35% aqueous solution of formaldehyde and 50.8 g of acetic acid. After the reaction, the solvent was evaporated. A saturated aqueous solution of sodium bicarbonate was added to the residue and the mixture was extracted with chloroform three times. The extract was dried with magnesium sulfate, the solvent evaporated, and the resulting yellow oil subjected to a column chromatography (500 g of silica gel being used; eluates were (1) ethylacetate/n-hexane in 3:1 proportions and (2) the same in 1:1 proportion). The isolated and purified product was recrystallized from methanol/water to give 23.33 g of pale yellow crystals, m.p. 98°-100° C. (methanol/water).

Workup

  1. temperatureheated
  2. customAfter the reaction
  3. customthe solvent was evaporated
  4. additionA saturated aqueous solution of sodium bicarbonate was added to the residue
  5. extractionthe mixture was extracted with chloroform three times
  6. dry with materialThe extract was dried with magnesium sulfate
  7. customthe solvent evaporated
  8. customThe isolated
  9. custompurified product
  10. customwas recrystallized from methanol/water

Sources & evidence

ORD record
ord-12f35c69fd054d26ba9ed4bef0d550e3
Source dataset
uspto-grants-1990_05
Patent number
US04927835

Reaction notes

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