Water → HCID 86597122, compound

HRID 1987330Notes

Reaction equation

HRID 1987330 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][OH:8])=[CH:4][N:3]=[CH:2]1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].CCN(CC)CC.O>C(Cl)Cl>[S:1]1[C:5]([CH2:6][CH2:7][O:8][S:10]([CH3:9])(=[O:12])=[O:11])=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 113895962-(thiazol-5-yl)ethanol

Product 1

HCID 86597122HCID 86597122, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a solution of 2-thiazol-5-yl-ethanol (0.154 g, 1.19 mmol) in CH2Cl2 (10 mL) was added MsCl (0.150 g, 1.31 mmol) and Et3N (0.180 g, 1.79 mmol). The mixture was stirred at room temperature for 1 h. Water (20 mL) was added, and the mixture was extracted with CH2Cl2 (3×30 mL). The extracts were combined and dried over Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (EtOAc), affording methanesulfonic acid 2-thiazol-5-yl-ethyl ester as a pale yellow liquid (0.246 g, 100%). 1H NMR(CDCl3) δ 2.99 (s, 3H), 3.33 (t, 2H, J=6.3 Hz), 4.42 (t, 2H, J=6.3 Hz), 7.73 (s, 1H), 8.74 (s, 1H).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration the solvent
  4. customwas removed by evaporation under vacuum
  5. customthe residue was purified by flash chromatography on a silica gel column (EtOAc)

Sources & evidence

ORD record
ord-cd3b80e349b44a4980ba4807a97dc6a4
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

Loading…