Potassium Carbonate → HCID 86722066, compound

HRID 1507764Notes

Reaction equation

HRID 1507764 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:14][C:15](=[O:35])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([C:27]#[C:28][Si](C)(C)C)[C:24]([Cl:33])=[C:23]([F:34])[CH:22]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH2:7]([O:14][C:15](=[O:35])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([F:34])[C:24]([Cl:33])=[C:25]([C:27]#[CH:28])[CH:26]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86722067HCID 86722067, compound

Product 1

HCID 86722066HCID 86722066, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (2.76 g, 20 mmol, 2 eq.) was added to a solution of 4a (4.50 g, 10.36 mmol, 1 eq.) in degassed MeOH (200 mL). The suspension was stirred at room temperature for 30 min. before concentration. The residue was partitioned between EtOAc (200 mL) and brine (200 mL). The EtOAc layer was separated and washed further with brine (100 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography (0-50%, EtOAc in heptane) to afford 5a as a colorless oil (3.60 g, 96%).

Workup

  1. customThe residue was partitioned between EtOAc (200 mL) and brine (200 mL)
  2. customThe EtOAc layer was separated
  3. washwashed further with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0-50%, EtOAc in heptane)

Sources & evidence

ORD record
ord-232ac167893947c1ba95204fefcc1d5b
Source dataset
uspto-grants-2015_12
Patent number
US09221827B2

Reaction notes

Loading…