2-Mercaptoethanol → HCID 54425911, compound

HRID 893144Notes

Reaction equation

HRID 893144 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-f26040a482484d4292396a793a30142c
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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