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

HRID 2108635Notes

Reaction equation

HRID 2108635 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 (MgSO4), 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. dry with materialthe combined organic extracts were dried (MgSO4)
  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-b6d15837304c434eb257db6493dbb59d
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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