Triethylamine → (S)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

HRID 1978407Notes

Reaction equation

HRID 1978407 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(=O)([O-])O.[Na+]>C(OCC)C>[CH3:20][S:21]([O:1][CH2:2][C@H:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 6541029(R)-2-(Hydroxymethyl)-1,4-benzodioxane

Product 1

HCID 11128529(S)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.410 g (2.467 mM) of (R)-2-hydroxymethyl-1,4-benzodioxane and 0.52 ml (3.70 mM) of triethylamine in 30 ml of diethyl ether was added 0.21 ml (2.71 mM) of methanesulfonyl chloride dropwise with ice-cooling and the mixture was stirred for 0.5 hour. This reaction mixture was poured in aqueous solution of sodium hydrogen carbonate and extracted with 2 portions of ethyl acetate. The organic layers were combined and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was passed through a short silica gel column (hexane-ethyl acetate=3/1 to 2/1) to provide crude (S)-2-methanesulfonyloxymethyl-1,4-benzodioxane.

Workup

  1. temperaturecooling
  2. extractionextracted with 2 portions of ethyl acetate
  3. dry with materialdried over MgSO4
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-749ad15eb049458480c433e1f282c4b9
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…