Tetrabutylammonium Fluoride → 5-(4-Hydroxy-2,6-dimethylbenzyl)-2-methoxymethoxybenzaldehyde

HRID 1170995Notes

Reaction equation

HRID 1170995 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([O:21][Si](C(C)C)(C(C)C)C(C)C)[CH:18]=[C:17]([CH3:32])[C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([CH:12]=1)[CH:10]=[O:11].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.O>[OH:21][C:19]1[CH:18]=[C:17]([CH3:32])[C:3]([CH2:4][C:5]2[CH:6]=[CH:7][C:8]([O:13][CH2:14][O:15][CH3:16])=[C:9]([CH:12]=2)[CH:10]=[O:11])=[C:2]([CH3:1])[CH:20]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866034575-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde

Product 1

HCID 866034585-(4-Hydroxy-2,6-dimethylbenzyl)-2-methoxymethoxybenzaldehydeYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-benzaldehyde (1.4 g, 3.07 mmol) in THF (15 mL) was added TBAF (1 M, 3.68 mL) at 0° C. After stirring at r.t. for 2 h, the reaction mixture was diluted with EtOAc and water. The water layer was extracted with EtOAc and the combined organic extracts were dried (NgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:9) to afford 5-(4-hydroxy-2,6-dimethylbenzyl)-2-methoxymethoxybenzaldehyde (590 mg, 64% for two steps): 1H NMR (200 MHz, CDCl3): δ 10.45 (s, 1H), 7.54 (s, 1H), 7.27 (m, 1H), 7.09 (m, 1H), 6.56 (s, 2H), 5.25 (s, 2H), 3.92 (s, 2H), 3.50 (s, 3H), 2.16 (s, 6H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.68.

Workup

  1. extractionThe water layer was extracted with EtOAc
  2. customthe combined organic extracts were dried (NgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate-hexanes; 1:9)

Sources & evidence

ORD record
ord-75de7dd4a5f243239800a4ebb917cb47
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

Loading…