Tetrahydrofuran → HCID 54002742, compound

HRID 341993Notes

Reaction equation

HRID 341993 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H](SC[C@@H](CC)C(O)=O)CCC4C=CC=CC=4C(O)(C)C)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.CO[C:43](=[O:46])[O:44][CH3:45].[H-].[Na+].[H][H].C1C[O:54][CH2:53][CH2:52]1>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:53](=[O:54])[CH2:52][C:43]([O:44][CH3:45])=[O:46])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:10][CH:11]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 53978197HCID 53978197, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54002742HCID 54002742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 500 mL flask fitted with a condenser were suspended the ketone of Step 2 (57.05 g, 185 mmol) and dimethylcarbonate (13.70 mL, 2.5 equiv.) in THF (230 mL). 80% NaH (16.70 g, 3 equiv.) was added portionwise over a few minutes and the reaction was initiated through the addition of MeOH (370 μl). The mixture was stirred at r.t. The solids gradually dissolved and when the evolution of hydrogen has subsided, the mixture was heated at 70° C. for 1 h. After cooling to r.t., it was poured onto cold 25% aq NH4OAc. The solid was collected and air dried and swished in EtOH (600 mL) containing EtOAc (50 mL) for 18 h. The title compound was collected as a pale beige solid (60.3 g, 89% yield).

Workup

  1. customIn a 500 mL flask fitted with a condenser
  2. dissolutionThe solids gradually dissolved
  3. temperaturethe mixture was heated at 70° C. for 1 h
  4. temperatureAfter cooling to r.t.
  5. customThe solid was collected
  6. customair dried
  7. additioncontaining EtOAc (50 mL) for 18 h

Sources & evidence

ORD record
ord-f6fd22b773ba4a048c5e6e2c2027b2ff
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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