HCID 178418689, compound → HCID 58196244, compound

HRID 2108660Notes

Reaction equation

HRID 2108660 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][PH:13](=[O:17])[O:14][CH2:15][CH3:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:18][Mg+].[Br-]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][P:13]([CH3:18])(=[O:17])[O:14][CH2:15][CH3:16])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 178418689HCID 178418689, compoundHCID 178476824HCID 178476824, compound

Product 1

HCID 58196244HCID 58196244, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the crude ethyl (4-methylphenyl)sulfonyloxymethylphosphinate monochloridate (2.00 g, 6.39 mmol) in dry THF (30.0 mL) at −78° C. was added MeMgBr (2.20 mL, 6.97 mmol, 3.0 M in diethyl ether). The reaction was quenched immediately after the MeMgBr addition with 1 mL of acetic acid. The reaction mixture was diluted with ethyl acetate and H2O and the organic layer was washed twice with saturated aqueous NaHCO3 and once with H2O. The organic layer was concentrated and coevaporated with MeOH. The product was obtained by precipitation from hexanes to afford the title compound as a white solid (1.40 g, 77% over two steps): 1H NMR (200 MHz, DMSO-d6): δ 7.85 (m, 2H), 7.52 (m, 2H), 4.30 (d, J=12.0 Hz, 2H), 3.90 (m, 2H), 2.40 (s, 3H), 1.45 (d, J=21.0 Hz, 3H), 1.15 (m, 3H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-methanol (9:1); Rf=0.27.

Workup

  1. customThe reaction was quenched immediately
  2. additionafter the MeMgBr addition with 1 mL of acetic acid
  3. additionThe reaction mixture was diluted with ethyl acetate and H2O
  4. washthe organic layer was washed twice with saturated aqueous NaHCO3 and once with H2O
  5. concentrationThe organic layer was concentrated
  6. customThe product was obtained by precipitation from hexanes

Sources & evidence

ORD record
ord-33556e9396b742d58258402d1a5f8b36
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

Loading…