Methanol → HCID 86739629, compound

HRID 2418018Notes

Reaction equation

HRID 2418018 reaction equation
CO[CH:3]=[CH:4][C:5](=[O:7])[CH3:6].[C:8]([O-])([O-])=[O:9].[K+].[K+].CO.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][SH:20]>O1CCCC1.CCOCC.O>[CH3:16][O:17][C:18]([O:9][CH3:8])([O:21][CH3:22])[CH2:19][S:20][CH2:3][CH2:4][C:5](=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 942973-Buten-2-one, 4-methoxy-HCID 148182602,2-Dimethoxyethane-1-thiol

Product 1

HCID 86739629HCID 86739629, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To a solution of 2.3 g. (18.9 mmol) of 4-methoxy-3-buten-2-one and 50 mg. K2CO3 in 15 ml. of methanol was added 1.88 g. (18.9 mmol) of 2-mercaptoacetaldehyde dimethyl acetal and the reaction mixture heated to reflux for 10 minutes. On cooling, the methanol was removed by rotatory evaporation, 25 ml. of ether was added and the solution was extracted with water, brine, and dried over anhydrous magnesium sulfate. Filtration and removal of solvent afforded 2.95 g. (70%) of water white oil homogeneous by TLC (SiO2), tetrahydrofuran/ether, 1:1; Mol. dist. 140° (0.2 mm Hg), 1H-NMR (CDCl3) delta 2.21 (s, 3), 2.66-3.11 (m, 4), 3.42 (s, 9), 4.44 (t, 1), 4.89 (doublet of doublets, 1); IR (film) cm-1 1710 (s).

Workup

  1. temperatureto reflux for 10 minutes
  2. temperatureOn cooling
  3. customthe methanol was removed by rotatory evaporation, 25 ml
  4. additionof ether was added
  5. extractionthe solution was extracted with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationFiltration and removal of solvent
  8. customafforded 2.95 g
  9. custom140° (0.2 mm Hg), 1H-NMR (CDCl3) delta 2.21 (s, 3), 2.66-3.11 (m, 4), 3.42 (s, 9), 4.44 (t, 1), 4.89 (doublet of doublets, 1)

Sources & evidence

ORD record
ord-1276ec8c354a40cf8f8146702bf9a8c3
Source dataset
uspto-grants-1984_09
Patent number
US04471139

Reaction notes

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