2-Mercaptoethanol → HCID 54425911, compound

HRID 1109411Notes

Reaction equation

HRID 1109411 reaction equation
[C:1]1([CH2:11][C:12](=[CH2:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[SH:25][CH2:26][CH2:27][OH:28]>C(OCC)C>[OH:28][CH2:27][CH2:26][S:25][CH2:18][CH:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 15672-Mercaptoethanol2×HCID 11776435HCID 11776435, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54425911HCID 54425911, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.04 g of ethyl 2-(1-naphthyl)methyl-2-propenoate was dissolved in 714 μl of 2-mercaptoethanol, and 102 mg of potassium tert-butoxide was added thereto at room temperature under stirring. The mixture was stirred at room temperature for 15 minutes. 500 μl of 2-mercaptoethanol was added thereto and the mixture was stirred for 15 minutes. Then, the reaction solution was diluted with 150 ml of diethyl ether. The diethyl ether layer was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 2.81 g of ethyl (2RS)-3-(2-hydroxyethyl)thio-2-(1-naphthylmethyl)propionate as colorless oily substance.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 minutes
  2. stirringthe mixture was stirred for 15 minutes
  3. washThe diethyl ether layer was washed with water and with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-8d2ddaa0ef8d4cf0940aa17a423b453f
Source dataset
uspto-grants-1994_06
Patent number
US05319082

Reaction notes

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