Tetrahydrofuran → HCID 11999707, compound

HRID 645914Notes

Reaction equation

HRID 645914 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:33])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[N:16]2[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:38]1COCC1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([O:33][CH3:38])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[N:16]2[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 68579670HCID 68579670, compound

Product 1

HCID 11999707HCID 11999707, compoundYield 75%

Procedure

To a solution of 6 (0.20 g, 0.43 mmol) in dry THF (3 mL) at 0° C., NaH (60%, 0.021 g, 0.86 mmol) was added. After the mixture was stirred for 30 min, Mel (54 μL, 0.86 mmol) was added and stirring was continued overnight at room temperature. The reaction was quenched by the addition of saturated aqueous NH4Cl (0.5 mL). Solvent was evaporated under reduced pressure and the residue was extracted with CH2Cl2 (2×10 mL). The combined organic layer was washed with H20 (3 mL), brine (3 mL) and then dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure and the residual red syrup was purified by column chromatography using 35% acetone/hexane as the eluent to provide 7 (0.16 g, 75%) as a light yellow syrup.

Workup

  1. additionMel (54 μL, 0.86 mmol) was added
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. customThe reaction was quenched by the addition of saturated aqueous NH4Cl (0.5 mL)
  5. customSolvent was evaporated under reduced pressure
  6. extractionthe residue was extracted with CH2Cl2 (2×10 mL)
  7. washThe combined organic layer was washed with H20 (3 mL), brine (3 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customSolvent was evaporated under reduced pressure
  10. customthe residual red syrup was purified by column chromatography

Sources & evidence

ORD record
ord-d4c105a3ebe0429cae4fab1b0ceb7391
Source dataset
uspto-grants-2010_04
Patent number
US07705021B2

Reaction notes

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