Tetrabutylammonium Fluoride → tert-Butyl [(2-fluoro-4-hydroxyphenyl)methyl]carbamate

HRID 1634818Notes

Reaction equation

HRID 1634818 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][C:10]=1[F:33])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:34])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:33])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69985694HCID 69985694, compound

Product 1

HCID 53439114tert-Butyl [(2-fluoro-4-hydroxyphenyl)methyl]carbamateYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-(t-butyl-diphenyl-silanyloxy)-2-fluoro-benzyl]-carbamic acid tert-butyl ester (2.1 g, 4.38 mmol) in 5 mL of THF was treated with tetrabutylammonium fluoride (4.5 ml of a 1M solution) and stirred at ambient temperature for 1 hour. The reaction was concentrated in vacuo and purified by flash chromatography (chloroform-methanol, 5:1) to give 0.46 g of the phenol.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by flash chromatography (chloroform-methanol, 5:1)

Sources & evidence

ORD record
ord-8668c853a4d34f8f9af379b27ce84657
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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