Tetrahydrofuran → HCID 54002742, compound

HRID 865460Notes

Reaction equation

HRID 865460 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-bef426a0109d4002974709d9333dfee1
Source dataset
uspto-grants-1996_10
Patent number
US05565473

Reaction notes

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