Trityl chloride → 2-((Triphenylmethyl)amino)ethanol

HRID 1734673Notes

Reaction equation

HRID 1734673 reaction equation
Cl.[CH2:2]([CH2:4][NH2:5])[OH:3].CCN(CC)CC.[C:13](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.CC#N.C(Cl)Cl>[C:13]([NH:5][CH2:4][CH2:2][OH:3])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 74819Ethanolamine Hydrochloride

Product 1

HCID 31256082-((Triphenylmethyl)amino)ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Ethanolamine hydrochloride (9.9 g; 100 mmol) is partially dissolved in CH2Cl2 /CH3CN (200 ml/100 ml) and Et3N (23 ml; 170 mmol) is then added. Tritylchloride (18.9 g; 67.6 mmol) is added portionwise over 30 minutes. After the addition is complete the reaction mixture is allowed to stir an additional 30 minutes, diluted with CH2Cl2, washed with H2O 2x and brine, dried (MgSO4), concentrated in vacuo and purified by column chromatography with silica/CH2Cl2 to give N-tritylethanolamine as an oil which is used directly in Step B.

Workup

  1. additionAfter the addition
  2. washwashed with H2O 2x and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography with silica/CH2Cl2

Sources & evidence

ORD record
ord-f812c3baedfa43ad936210cfa2035df8
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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