Methanesulfonyl chloride → HCID 58556972, compound

HRID 1044051Notes

Reaction equation

HRID 1044051 reaction equation
[OH:1][CH:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CCN(C(C)C)C(C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:1][CH:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride3×HCID 81531Diisopropylethylamine3×HCID 12266229Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate

Product 1

HCID 58556972HCID 58556972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate (I26) (4.58 g, 24.6 mmol) was dissolved in dry DCM (125 ml) and cooled at 0° C. DIPEA (5.15 ml, 29.5 mmol) and methanesulphonyl chloride (2.11 ml, 27.1 mmol) were added, and the resulting solution was stirred at room temperature for 1 hour. DIPEA (0.86 ml, 4.92 mmol) and methanesulphonyl chloride (0.19 ml, 2.46 mmol) were added again. After 1 additional hour, a third portion of DIPEA (0.43 ml, 2.46 mmol) and methanesulphonyl chloride (77 ul, 0.98 mmol) was added. After 1 hour, the reaction was completed. The mixture was diluted with DCM, washed with sat. NaHCO3, water and brine, dried (Na2SO4), filtered, and evaporated. The resulting oil was used for the next step without any further purification.

Workup

  1. waitAfter 1 hour
  2. washwashed with sat. NaHCO3, water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was used for the next step without any further purification

Sources & evidence

ORD record
ord-8392a2684bb24921b9b4e24feed42829
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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