Ethanolamine → HCID 21894500, compound

Participants

Reaction Steps

To 200 mL of dichloromethane was added 100 mmole of ethanolamine, 200 mmole of N-methylmorpholine and 105 mmole of ethyltrifluoroacetate. This solution was allowed to stir for 30 minutes and then 105 mmol of triphenylmethyl chloride was added. After stirring overnight, the solution was transferred to a separatory fennel and washed twice with water. The organic layer was dried with sodium sulfate, filtered and evaporated to a yellow oil. The product was determined to be impure and was redissolved in DCM and washed with 5% monobasic sodium phosphate and then a mixture of 10% citric acid and 5% monobasic sodium phosphate. The organic layer was dried with sodium sulfate, filtered and evaporated to a yellow oil. The residue was crystallized from methanol but this caused the impurity to crystallize. The mother liquor was then recrystallized from hexanes/ethyl acetate to yield 9.0 g of crystaline N-(trifluoroacetyl)-O-(trityl)-ethanolamine.

Provenance & Evidence