Methanesulfonyl chloride → HCID 86650639, compound

HRID 1623392Notes

Reaction equation

HRID 1623392 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][CH:6]([CH2:8][OH:9])[CH2:5][O:4][CH2:3]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:6]1[CH2:5][O:4][CH2:3][C:2]([CH3:10])([CH3:1])[O:7]1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 669371811263375-44-5

Product 1

HCID 86650639HCID 86650639, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (0.52 mL, 3.74 mmol) and (6,6-dimethyl-1,4-dioxan-2-yl)methanol (390 mg, 2.67 mmol) were dissolved in DCM (10 mL). Methanesulfonyl chloride (0.249 mL, 3.20 mmol) was slowly added at 0° C. After the addition was completed 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 (584 mg, 98%). 1H NMR (400 MHz, CDCl3) δ ppm 4.00-4.09 (3H, m), 3.74 (1H, dd, J=11.2, 2.8 Hz), 3.42 (1H, d, J=11.6 Hz), 3.16-3.23 (2H, m), 2.99 (3H, s), 1.27 (3H, s), 1.05 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-4758fe2eb511498a9540587c09ddb5fb
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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