Tetrabutylammonium Fluoride → 3-(2-Benzyloxymethyl-4-hydroxy-phenyl)-propionic acid tert-butyl ester

HRID 1181129Notes

Reaction equation

HRID 1181129 reaction equation
[C:1]([O:5][C:6](=[O:42])[CH2:7][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[CH2:33][O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:42])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:33][O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589794353-[2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

Product 1

HCID 589791133-(2-Benzyloxymethyl-4-hydroxy-phenyl)-propionic acid tert-butyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL round bottomed flask was charged with 3-[2-benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester (1.03 g, 1.77 mmol), anhydrous THF (60 mL), and then tetrabutylammonium fluoride (5.3 mL, 5.3 mmol, 1.0 M in THF). The reaction mixture was stirred under a nitrogen atmosphere for 1 h, concentrated, and diluted with EtOAc (100 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to give an oil. The crude oil was purified using radial chromatography (EtOAc:hexanes 10:90 to 50:50) to give a white solid (0.52 g, 86%). MS (ES) m/e 343 (M−1).

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give an oil
  7. customThe crude oil was purified

Sources & evidence

ORD record
ord-730e7781c61b487e84986ff223b5c51a
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

Loading…