2-Mercaptoethanol → HCID 14958432, compound

Participants

Reaction Steps

tert-butyl bromoacetate 1 (15 g, 0.077 mol, 1 eqv.) and triethylamine (16 g, 0.16 mol, 2 eqv.) were dissolved in CH2Cl2 (100 mL) under nitrogen and cooled to 0 C. 2-mercaptoethanol (6.3 g, 0.081 mol, 1.05 eqv.) was slowly added to the mixture and the reaction mixture was warmed to room temperature. The reaction was stirred for 1 additional hour. Completion of the reaction was monitored by TLC (ethylacetate (EtOAc):hexane (Hex), 1:1 (v/v), Rf: 0.88). Base and acid extractions were carried out with 1M KCO3, pH 10 and 1M NaOAc pH 3.5, twice, respectively. The combined organic layers were washed with brine, dried with MgSO4 and filtered through Ø 185 mm whatman filter papers. The filtrate was concentrated in vacuo (CH2Cl2) to obtain 9.2 g (62% yield) 2 as a colourless oil.

Provenance & Evidence