Benzoyl chloride → HCID 121396370, compound

HRID 60743Notes

Reaction equation

HRID 60743 reaction equation
[OH:1][C@H:2]([C@H:5]1[O:9][C:8](=[O:10])[C@H:7]([CH3:11])[CH2:6]1)[CH2:3][CH3:4].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:12]([O:1][C@H:2]([C@@H:5]1[CH2:6][C@@H:7]([CH3:11])[C:8](=[O:10])[O:9]1)[CH2:3][CH3:4])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 121396379HCID 121396379, compound2×

Product 1

HCID 121396370HCID 121396370, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (3R,5S)-5-[(1S)-1-hydroxypropyl]-3-methyl-tetrahydrofuran-2-one (compound 28g, 1.0 g, 6.3 mmol), TEA (3.2 g, 31.2 mmol) and DMAP (100 mg) in DCM (50 mL) was added benzoyl chloride (1.8 g, 12.6 mmol) slowly at 0° C. The mixture was stirred at 25° C. for 4 hours and then quenched by saturated NaHCO3 solution, extracted with EtOAc (100 mL) twice. The organic layers were combined, washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:5 EtOAc in petroleum ether) to afford 1.4 g of [(1S)-1-[(2S,4R)-4-methyl-5-oxo-tetrahydrofuran-2-yl]propyl] benzoate (compound 28h) as a colourless oil.

Workup

  1. customquenched by saturated NaHCO3 solution
  2. extractionextracted with EtOAc (100 mL) twice
  3. washwashed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 1:20 to 1:5 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-82e2d0f445584af898490c99f48cb4fe
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…