Methanesulfonyl chloride → Pent-4-yn-1-yl methanesulfonate

HRID 1633686Notes

Reaction equation

HRID 1633686 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH3:7][S:8](Cl)(=[O:10])=[O:9].C(N(CC)C(C)C)(C)C.OS([O-])(=O)=O.[K+]>C(Cl)Cl.O>[CH2:1]([O:6][S:8]([CH3:7])(=[O:10])=[O:9])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 793464-Pentyn-1-olHCID 81531DiisopropylethylamineHCID 516920Potassium bisulfate

Product 1

HCID 12476209Pent-4-yn-1-yl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

4 ml (43.2 mmol) 4-pentyn-1-ol in 140 ml CH2Cl2 were treated with 3.7 ml (47.6 mmol) methanesulfonyl chloride and 11.1 ml (64.84 mmol) N,N-diisopropylethylamine at 0° C. for 10 min. The solution was stirred at RT for 1 h and was diluted with CH2Cl2. Water was added, the mixture was stirred for 10 min and was added to a 10% aqueous KHSO4 solution. The phases were separated and the aqueous phase was extracted with CH2Cl2. The combined organic ones were washed with a saturated aqueous solution of NaHCO3 and brine, dried over Na2SO4 and evaporated to give crude Methanesulfonic acid pent-4-ynyl ester as yellow oil, MS: 156 (MH+).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. washThe combined organic ones were washed with a saturated aqueous solution of NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-cbe6e5f132e14981b676a1970808c189
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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