Methanol → HCID 131713684, compound

HRID 1632594Notes

Reaction equation

HRID 1632594 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][SH:5].[C:8]([O-:11])([O-])=[O:9].[K+].[K+].C([O:17][C:18](=[CH2:22])[C:19](=O)[CH3:20])(=O)C.[CH3:23]O>>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH:4]([S:5][CH2:20][CH2:19][C:18](=[O:17])[CH3:22])[O:11][C:8](=[O:9])[CH3:23]

Participants

5

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 11073438HCID 11073438, compoundHCID 148182602,2-Dimethoxyethane-1-thiol

Product 1

HCID 131713684HCID 131713684, compound

Procedure

To a solution of 15 g. (0.123 mol) of 2-mercaptoacetaldehyde dimethylacetal in 150 ml. of methanol was added 225 mg. of K2CO3 and 15.8 g. (0.123 mol) of 3-acetoxy-3-buten-2-one. After 2 hours at ambient temperature, the solvent was removed in vacuo, the oily residue dissolved in ether, washed with water and dried over Na2SO4. Filtration and removal of solvent in vacuo afforded 24.9 g. (81%) of the crude product: 1H-NMR (CDCl3) delta 2.15 (s, 3), 2.19 (s, 3), 2.74 (d, 2, J=5.4 Hz), 3.03 (m, 2), 3.34 (s, 6), 4.50 (t, 1, J=5.4 Hz), 5.22 (d of d, 1); 13C-NMR (CDCl3) delta 203.5 (s), 169.7 (s), 104.6 (d), 77.5 (d), 53.5 (q), 53.3 (g), 34.5 (d), 32.4 (t), 26.6 (q), 20.3 (q); mass spectrum (70 eV) m/e 250.0855 (parent, calcd. for C10H18O5S; 250.1134); IR (film) cm1 1747 (s), 1733 (s).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe oily residue dissolved in ether
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and removal of solvent in vacuo
  6. customafforded 24.9 g

Sources & evidence

ORD record
ord-c62dc3baba584d66aa6c5a5d632147ea
Source dataset
uspto-grants-1984_10
Patent number
US04476312

Reaction notes

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