Methanol → HCID 86739629, compound

HRID 1632597Notes

Reaction equation

HRID 1632597 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-17d03af49c9e4cf7b064ad5369fc7a06
Source dataset
uspto-grants-1984_10
Patent number
US04476312

Reaction notes

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