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

HRID 990835Notes

Reaction equation

HRID 990835 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-e91dc26186ae45a39849502830f3981c
Source dataset
uspto-grants-2002_10
Patent number
US06462055B2

Reaction notes

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