Hydrochloric Acid → trityloxy-acetic Acid Ethyl Ester

HRID 1776552Notes

Reaction equation

HRID 1776552 reaction equation
Cl[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>C(Cl)Cl>[C:2]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 12184Ethyl Glycolate

Product 1

HCID 12230788trityloxy-acetic Acid Ethyl EsterYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (chloromethanetriyl)tribenzene (9.8 g, 35.2 mmol) in DCM (500 ml), ethyl 2-hydroxyacetate (4.33 ml, 45.7 mmol) and Py (3.70 ml, 45.7 mmol) were added at RT. The reaction was heated at 50° C. for 9 hours. HCl 2N was added to the mixture, and the organic phase was separated, dried over Na2SO4 and evaporated under vacuum. The resulting white solid was triturated in Hexane. Ethyl 2-(trityloxy)acetate was obtained (8.2 g, 23.67 mmol, 67.3% yield) and used in the following step without further purification.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customThe resulting white solid was triturated in Hexane

Sources & evidence

ORD record
ord-e07fa50800ff44a796b3236562ab945d
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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