Triethylamine → 5-(Thiophen-2-yl)pent-4-ynyl methanesulfonate

HRID 1971645Notes

Reaction equation

HRID 1971645 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]#[C:7][CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl.O>[CH3:19][S:20]([O:11][CH2:10][CH2:9][CH2:8][C:7]#[C:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9989594HCID 9989594, compound

Product 1

HCID 581248695-(Thiophen-2-yl)pent-4-ynyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 145 mg of 2a and 200 μl of triethyl amine in 2 ml of dichloromethane was added dropwise at 0° C. 80 μl of methanesulfonyl chloride in 1 ml of dichloromethane. The reaction mixture was stirred for ½ hr and then diluted with 10 ml of water and extracted with dichloromethane. The organic layer was washed with 1M K2CO3, dried and concentrated, to provide 210 mg of essentially pure 2b as an oil; Rf (heptane/ethyl acetate 1/1) 0.55. NMR (CDCl3): δ 2.03 (m, 2, CH2), 2.60 (t, 2, CH2), 4.40 (t, 2, CH2), 3.03 (s, 3, CH3SO2), 6.95, 7.13, 7.20 (3×m, 3, thiophene-H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with 1M K2CO3
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89bcba891e8d43f2a5210be4328d4ffe
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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