Sodium Chlorite → HCID 90303344, compound

HRID 1051933Notes

Reaction equation

HRID 1051933 reaction equation
[CH:1]([Si:4]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[C:5]1[S:6][C:7]2[CH:12]([CH2:13][OH:14])[CH2:11][O:10][C:8]=2[N:9]=1)([CH3:3])[CH3:2].[O-:21]Cl=O.[Na+]>C(Cl)Cl.O>[CH:18]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:15]([CH3:17])[CH3:16])[C:5]1[S:6][C:7]2[CH:12]([C:13]([OH:21])=[O:14])[CH2:11][O:10][C:8]=2[N:9]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 23668197Sodium ChloriteHCID 90303362HCID 90303362, compound

Product 1

HCID 90303344HCID 90303344, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A soln. of (2-(triisopropylsilyl)-5,6-dihydrofuro[2,3-d]thiazol-6-yl)methanol (1.77 g, 5.64 mmol)) in DCM (56 mL) was treated at 0° C. with DMP (2.87 g, 6.77 mmol) portionwise over 1 h. The mixture was stirred at 0° C. for 2 h, then, it was allowed to warm to RT and stirred for 2 h. Subsequently, the mixture was quenched with aq. sat. Na2S2O3 and aq. sat. NaHCO3 and was extracted with DCM. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. The residue was dissolved in tert-BuOH (16 mL) and 2-methyl-2-butene (4 mL) and treated at 0° C. dropwise over 30 min with a soln. of NaH2PO4 (2.64 g, 16.9 mmol) and NaClO2 (0.96 g, 8.46 mmol) in H2O (5 mL). The mixture was stirred at RT for 45 min, then, the volatiles were removed in vacuo, the residue was diluted with H2O and extracted with EtOAc. The comb. org. layers were dried over MgSO4 and conc. in vacuo.

Workup

  1. temperatureto warm to RT
  2. stirringstirred for 2 h
  3. customSubsequently, the mixture was quenched with aq. sat. Na2S2O3 and aq. sat. NaHCO3
  4. extractionwas extracted with DCM
  5. washlayers were washed with brine
  6. dry with materialdried over MgSO4
  7. dissolutionThe residue was dissolved in tert-BuOH (16 mL)
  8. addition2-methyl-2-butene (4 mL) and treated at 0° C. dropwise over 30 min with a soln
  9. stirringThe mixture was stirred at RT for 45 min
  10. customthe volatiles were removed in vacuo
  11. additionthe residue was diluted with H2O
  12. extractionextracted with EtOAc
  13. dry with materiallayers were dried over MgSO4 and conc. in vacuo

Sources & evidence

ORD record
ord-6eed2356bdcd4a1db923338fc56ee88f
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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