Methanesulfonyl chloride → HCID 86690733, compound

HRID 1473915Notes

Reaction equation

HRID 1473915 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:5]=2[CH2:4][O:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C1COCC1.CCOC(C)=O>[CH3:16][S:17]([O:14][CH2:13][CH2:12][C:11]1[C:5]2[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C:6]=2[CH:8]=[CH:9][CH:10]=1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86690731HCID 86690731, compound

Product 1

HCID 86690733HCID 86690733, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethanol (400 mg, 1.92 mmol, 1 eq.) in THF (20 mL) were added MsCl (438 mg, 3.84 mmol, 2.0 eq.) and TEA (0.8 mL, 5.76 mmol, 3.0 eq.) at rt. The mixture was stirred at rt for 1 h and diluted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated to give 2-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-5-yl)ethyl methanesulfonate (400 mg, crude) as a pale brown oil, which was used for next step without purification.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-893540a8d7874b3cba1d53a62973ade5
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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