Tetrabutylammonium Fluoride → 1-(4-Amino-2-chlorophenyl)ethanol

HRID 1385227Notes

Reaction equation

HRID 1385227 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[Si](C)(C)CCOC(=O)[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([OH:34])[CH3:33])=[C:28]([Cl:35])[CH:27]=1>O1CCCC1>[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([OH:34])[CH3:33])=[C:28]([Cl:35])[CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54096646[3-Chloro-4-(1-hydroxy-ethyl)-phenyl]carbamic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 185436011-(4-Amino-2-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (5.7 mL) is added to [3-chloro-4-(1-hydroxy-ethyl)-phenyl]-carbamic acid 2-trimethylsilanyl-ethyl ester (0.5 g) and the mixture is stirred at room temperature for approximately 3.5 hours. The solution is then concentrated under reduced pressure, dissolved in a 1:1 mixture of ethyl acetate and hexanes, washed successively with water then saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure followed by chromatography over silica gel (40% ethyl acetate in hexanes is used as the eluant) provides the product as an amber oil.

Workup

  1. concentrationThe solution is then concentrated under reduced pressure
  2. dissolutiondissolved in a 1:1 mixture of ethyl acetate and hexanes
  3. washwashed successively with water
  4. dry with materialsaturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-789b54d17c43469b9c4f720118bf1aa8
Source dataset
uspto-grants-2001_07
Patent number
US06262090B1

Reaction notes

Loading…