Methyl iodide → HCID 86761237, compound

HRID 2265238Notes

Reaction equation

HRID 2265238 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH3:19])[C@@H:10]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:20]I>CN(C=O)C.O>[CH3:20][O:12][C:11](=[O:13])[C@H:10]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:19]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 86761238HCID 86761238, compound

Product 1

HCID 86761237HCID 86761237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Jones reagent was prepared by mixing chromium (VI) oxide (2.87 g, 28.7 mmol), sulfuric acid (2.44 mL), and water (9.5 mL) for 10 min. The solution was used directly, and was added dropwise to a solution of (2R,3R)-3-(3,4-dichloro-phenyl)-2-methanesulfonyloxy-butan-1-ol (1.50 g, 4.79 mmol) in acetone (100 mL). After 4 h, isopropanol (9 mL) was added and the mixture was concentrated. Water was added, and the aqueous layer was extracted with DCM (3×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to give the crude acid. To a solution of (2R,3R)-3-(3,4-dichloro-phenyl)-2-methanesulfonyloxy-butyric acid (1.57 g, 4.80 mmol) in DMF (20 mL) were added KHCO3 (1.44 g, 14.4 mmol) and MeI (0.90 mL, 14.4 mmol). After 12 h, the mixture was diluted with water and extracted with EtOAc (2×), and the combined organic phases were washed with brine, dried (MgSO4) and concentrated. The product was purified by flash chromatography to give 1.13 g (69% over 2 steps) of the desired product. 1H NMR (400 MHz, CDCl3): 7.38 (d, J=8.3, 1H), 7.31 (d, J=2.1, 1H), 7.08 (dd, J=8.3, 2.1, 1H), 5.14 (d, J=4.7, 1H), 3.73 (s, 3H), 3.47-3.43 (m, 1H), 3.07 (s, 3H), 1.43 (d, J=7.2, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-1c85d3683f7a4d1bab8ef285482885e7
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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