Sodium ethoxide → HCID 14405955, compound

HRID 1650254Notes

Reaction equation

HRID 1650254 reaction equation
[O-]CC.[Na+].[Na].C([S:9][CH2:10][CH:11]1[O:15][C:14]([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:13][CH2:12]1)(=O)C>C(O)C>[SH:9][CH2:10][CH:11]1[O:15][C:14]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])([CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[S:13][CH2:12]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14405954HCID 14405954, compound

Product 1

HCID 14405955HCID 14405955, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium ethoxide in ethanol (20 mls) [prepared from 0.16 g (0.006 g-atom) of sodium metal] and the thioacetate produced in Example 63 (2.1 g, 0.0055 mol) was stirred for one hour at room temperature under nitrogen. Ethanol was removed in vacuo on the rotary evaporator and the residue dissolved in ethyl acetate. This organic phase was washed with 0.5N sodium bisulfate solution and dried over sodium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator to give 1.97 g (95%) of the title compound as an oil.

Workup

  1. customEthanol was removed in vacuo on the rotary evaporator
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThis organic phase was washed with 0.5N sodium bisulfate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationThe drying agent was filtered
  6. concentrationthe filtrate concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-2a3af9f2c72a4113989ca27a1d9064ac
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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