Methanesulfonyl chloride → HCID 86650641, compound

HRID 1963947Notes

Reaction equation

HRID 1963947 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][O:6][CH:5]([CH2:8][OH:9])[CH2:4][O:3]1.[CH3:11][S:12](Cl)(=[O:14])=[O:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:11][S:12]([O:9][CH2:8][CH:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[CH2:7][O:6]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66936837(5,5-Dimethyl-1,4-dioxan-2-yl)methanol

Product 1

HCID 86650641HCID 86650641, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5,5-Dimethyl-1,4-dioxan-2-yl)methanol (740 mg, 5.06 mmol) and TEA (0.988 mL, 7.09 mmol) were dissolved in DCM (20 mL). At 0° C. MsCl (0.473 mL, 6.07 mmol) was added dropwise. After the addition the solution was warmed to ambient temperature and stirred for 1 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous layer was extracted three times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1) to give the product as a colorless oil (805 mg, 71%). 1H NMR (400 MHz, CDCl3) δ ppm 4.18-4.19 (2H, m), 3.71-3.76 (1H, m), 3.66 (1H, t, J= 10.8 Hz), 3.52-3.57 (2H, m), 3.37 (1H, d, J= 11.6 Hz), 3.03 (3H, s), 1.28 (3H, s), 1.09 (3H, s).

Workup

  1. customAt 0° C
  2. additionAfter the addition the solution
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted three times with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 4:1 to 1:1)

Sources & evidence

ORD record
ord-68f0e23af6aa4ffabf90e83e3f4453db
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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