Sodium Thiosulfate → HCID 86650637, compound

HRID 1623390Notes

Reaction equation

HRID 1623390 reaction equation
[CH2:1]([O:4][CH2:5][C:6]([CH3:9])([OH:8])[CH3:7])[CH:2]=[CH2:3].C1C=C(Cl)C=C(C(OO)=[O:18])C=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:7][C:6]([OH:8])([CH3:9])[CH2:5][O:4][CH2:1][CH:2]1[CH2:3][O:18]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86650638HCID 86650638, compound

Product 1

HCID 86650637HCID 86650637, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(Allyloxy)-2-methylpropan-2-ol (1.50 g, 11.5 mmol) was dissolved in DCM (50 mL) and cooled to 0° C. mCPBA (77% max, 9.94 g) was added. The suspension was stirred at 0° C. for 6.5 hr. and then saturated NaHCO3 solution (˜20 ml) and Na2S2O3 solution (˜20 ml) were added. The resulting mixture was stirred at 0° C. for 15 min and the two layers were separated. The aqueous layer was extracted twice with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2) to give the product as a colorless oil (620 mg, 37%). 1H NMR (400 MHz, CDCl3) δ ppm 3.64 (1H, ddd, J=12.0, 5.2, 2.8 Hz), 3.24-3.29 (1H, m), 3.17-3.21 (1H, m), 3.11-3.14 (1H, m), 2.97-3.00 (1H, m), 2.88 (1H, br s), 2.60-2.64 (1H, m), 2.44-2.47 (1H, m), 1.02 (6H, s).

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred at 0° C. for 15 min
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted twice with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2)

Sources & evidence

ORD record
ord-09e7d63b125c4be7a0bdd2410bb04934
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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