Tetrabutylammonium Fluoride → HCID 86603462, compound

HRID 2108648Notes

Reaction equation

HRID 2108648 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:20]([CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])(=[O:22])=[O:21])[CH:5]=[C:6]([CH3:19])[C:7]=1[O:8][Si](C(C)C)(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:19][C:6]1[CH:5]=[C:4]([S:20]([CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])(=[O:22])=[O:21])[CH:3]=[C:2]([CH3:1])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86603461HCID 86603461, compound

Product 1

HCID 86603462HCID 86603462, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution diethyl (3,5-dimethyl-4-triisopropylsilanyloxy-benzenesulfonyl)methylphosphonate in THF (3 mL) at room temperature was added TBAF (0.3 mL, 1 M in THF). It was stirred at room temperature for 2 hrs. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (5:1) to afford diethyl (3,5-dimethyl-4-hydroxybenzenesulfonyl)methylphosphonate as a light yellow oil (70 mg, 100%): 1H NMR (300 MHz, CDCl3-d6): δ 7.54 (s, 2 H), 4.12 (m, 4 H), 3.65 (d, J=16.8 Hz, 2 H), 2.22 (s, 6 H), 1.22 (d, J=7.2 Hz, 6 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (5:1); Rf=0.44.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate-hexanes (5:1)

Sources & evidence

ORD record
ord-1066540d57a74a0190c2d5eb58c0bf19
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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