Tetrahydrofuran → HCID 44543251, compound

HRID 2354556Notes

Reaction equation

HRID 2354556 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]3[N:10]=[C:11]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]4[C:18](=[O:20])[C:19]=3[C:6]=2[CH2:5][CH2:4][C:3]=1[CH:21]=[O:22].CC(=CC)C.C1C[O:31]CC1.[O-]Cl=O.[Na+]>CC(O)(C)C.O>[Cl:1][C:2]1[C:7]2[S:8][C:9]3[N:10]=[C:11]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][N:12]4[C:18](=[O:20])[C:19]=3[C:6]=2[CH2:5][CH2:4][C:3]=1[C:21]([OH:31])=[O:22]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 105532-Methyl-2-buteneHCID 785255HCID 785255, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 44543251HCID 44543251, compound

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

Compound 4a (335 mg, 1.00 mmol) and 2-methyl-2-butene (1.06 ml, 10.01 mmol) were dissolved into 50 ml THF. A freshly prepared solution of 80% NaClO2 (339 mg, 3.00 mmol) and NaH2PO4.H2O (414 mg, 3.00 mmol) in 55 ml of t-BuOH/H2O 5:1 was added. The reaction mixture was stirred in room temperature for 6 hours. The reaction was quenched with water and extracted CH2Cl2. The organic phase was extracted with sat. NaHSO4. The water phase was then made acidic with HCl and extracted with CH2Cl2. the organic layer was washed with brine and dried over Na2SO2. After filtration the solvent was evaporated ant the product recrystallized from ethanol.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted CH2Cl2
  3. extractionThe organic phase was extracted with sat. NaHSO4
  4. extractionmade acidic with HCl and extracted with CH2Cl2
  5. washthe organic layer was washed with brine
  6. dry with materialdried over Na2SO2
  7. filtrationAfter filtration the solvent
  8. customwas evaporated ant the product
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c4b9da711e7e40a383366369e2a2dfc3
Source dataset
uspto-grants-2010_07
Patent number
US07754709B2

Reaction notes

Loading…