HCID 67500209, compound → HCID 9942256, compound

HRID 661367Notes

Reaction equation

HRID 661367 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([OH:12])[CH2:9][CH2:8][C:3]21[O:7][CH2:6][CH2:5][O:4]2>C(Cl)Cl>[CH3:1][CH:2]1[CH2:11][C:10](=[O:12])[CH2:9][CH2:8][C:3]21[O:4][CH2:5][CH2:6][O:7]2

Participants

3

Reactant 1

HCID 67500209HCID 67500209, compound

Product 1

HCID 9942256HCID 9942256, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 200 mL round bottom flask containing the product of Example 32C (1.50 g, 8.71 mmol) and DMP (4.06 g, 9.58 mmol) (Aldrich) was added methylene chloride (100 mL) and the reaction mixture was stirred for 1 hr at room temperature. The reaction mixture was quenched with saturated NaHCO3 and extracted with EtOAc (200 mL), dried (NaSO4), filtered, and concentrated in vacuo. The residue was purified on SiO2 with hexane/ethylacetate 0-20% to afford a colorless oil (1.12 g) in 76% yield. 1H NMR (300 MHz, CDCl3) δ ppm 4.20-3.95 (m, 4H), 2.63-1.97 (m, 6H), 1.94-1.74 (m, 1H), 1.04-0.83 (m, 3H). MS (DCI+) M/Z 171 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc (200 mL)
  3. dry with materialdried (NaSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on SiO2 with hexane/ethylacetate 0-20%

Sources & evidence

ORD record
ord-183c682852544a5191aa45834465d091
Source dataset
uspto-grants-2011_12
Patent number
US08084616B2

Reaction notes

Loading…