Trityl chloride → 566949-46-0

HRID 23718Notes

Reaction equation

HRID 23718 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[C:6]1([C:12](Cl)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]([C:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 80162-(Methylamino)ethanolHCID 8471Triethylamine

Product 1

HCID 5080555566949-46-0Yield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methylamino-ethanol (5.0 gr, 66.6 mmol) and triphenylmethyl chloride (18.6 g, 66.6 mmol) in 150 mL of CH2Cl2 was treated with triethylamine (9.3 mL, 66.6 mmol) and stirred at room temperature for 2 h. The solvent was removed in vacuum and the residue was dissolved in EtOAc (200 mL). The organic solution was washed with water (100 mL) and brine (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with 20% EtOAc in n-heptane, and those fractions with Rf=0.5 by TLC (EtOAc/hexane, 3/7) were combined and concentrated in vacuo to give 18.7 g of the product as a white solid.

Workup

  1. customThe solvent was removed in vacuum
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washThe organic solution was washed with water (100 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge
  8. washeluting with 20% EtOAc in n-heptane
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f4d88e62c3f40da9f45e3d3b29933b6
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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