Benzoyl chloride → HCID 90961573, compound

HRID 1357511Notes

Reaction equation

HRID 1357511 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C@@:11]1([C:19]([O:21][CH3:22])=[O:20])[CH2:17][C@@H:16]([OH:18])[C@@H:15]2[C@@H:13]([O:14]2)[CH2:12]1.C(N(CC)CC)C>ClCCl>[C:1]([O:18][C@H:16]1[C@@H:15]2[C@@H:13]([O:14]2)[CH2:12][C@:11]([OH:10])([C:19]([O:21][CH3:22])=[O:20])[CH2:17]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 91197364HCID 91197364, compound

Product 1

HCID 90961573HCID 90961573, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.216 mL, 1.86 mmol) was added dropwise to a 0° C. solution of Example 17C (0.35 g, 1.86 mmol) and triethylamine (0.52 mL, 3.74 mmol) in dichloromethane (20 mL). The reaction mixture was stirred overnight at room temperature, washed with saturated NaHCO3 solution, brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash column chromatography using hexanes/ethyl acetate (3/2) to afford 495 mg (91%) of the desired product as a colorless oil.

Workup

  1. washwashed with saturated NaHCO3 solution, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography

Sources & evidence

ORD record
ord-c196d0e2d9f6453d870b9b284b931658
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

Loading…