Water → 3-Thiopheneethanol methanesulfonate

HRID 2199570Notes

Reaction equation

HRID 2199570 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[S:6]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7]1.CCN(CC)CC.O>C(Cl)Cl>[CH3:1][S:2]([O:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][S:6][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 83731Thiophene-3-ethanol

Product 1

HCID 144229343-Thiopheneethanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methylsulfonyl chloride (2.22 ml, 28.75 mmol) was added dropwise to a solution of 3-thiopheneethanol (2.46 g, 19.2 mmol) and Et3N (5.3 ml) in DCM (50 ml) as 0° C. The mixture was stirred for 15 min before DCM and water was added. Organic phase was separated and residue purified by flash chromatography using 20-25% EtOAc in iso-hexane as eluents. Yield: 3.93 g (99%); colourless oil. HPLC: RT=2.20 min, 96% (254 nm, 10-90% MeCN in 0.1% TFA, 3 min ACE). 1H NMR (400 MHz, CDCl3): δ 2.90 (s, 3H), 3.13 (t, J 6.8 Hz, 2H), 4.44 (t, J 6.8 Hz, 2H), 7.00-7.02 (m, 1H), 7.11-7.12 (m, 1H), 7.32-7.36 m, 1H).

Workup

  1. additionwas added
  2. customOrganic phase was separated
  3. customresidue purified by flash chromatography
  4. customHPLC: RT=2.20 min, 96% (254 nm, 10-90% MeCN in 0.1% TFA, 3 min ACE)

Sources & evidence

ORD record
ord-d5286f6b6144454a80f91724dea4ccd3
Source dataset
uspto-grants-2016_06
Patent number
US09359311B2

Reaction notes

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