Sodium Thiosulfate → HCID 86650640, compound

HRID 1963945Notes

Reaction equation

HRID 1963945 reaction equation
[CH2:1]([O:4][C:5]([CH3:9])([CH3:8])[CH2:6][OH: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>[CH3:8][C:5]([O:4][CH2:1][CH:2]1[CH2:3][O:18]1)([CH3:9])[CH2:6][OH:7]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 71742286HCID 71742286, compound

Product 1

HCID 86650640HCID 86650640, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(allyloxy)-2-methylpropan-1-ol (2.37 g, 18.2 mmol) was dissolved in DCM (70 mL) and cooled to 0° C. mCPBA (77% max, 15.71 g) was added. The suspension was stirred at 0° C. for 6.5 hr before saturated NaHCO3 solution and Na2S2O3 solution were added. It 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 (910 mg, 34%). 1H NMR (400 MHz, CDCl3) δ ppm 3.65 (1H, dd, J= 11.2, 2.8 Hz), 3.47 (1H, br s), 3.31-3.41 (3H, m), 3.07-3.09 (1H, m), 2.74 (1H, t, J= 4.8 Hz), 2.63-2.65 (1H, m), 1.12 (6H, s).

Workup

  1. additionwas added
  2. additionwere added
  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-c7ada6231fd441b69123a4f451c47649
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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