Triethylamine → 4-Ethynylbenzyl methanesulfonate

HRID 539512

Reaction equation

HRID 539512 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[CH:2].C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>C(Cl)Cl>[CH3:21][S:18]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([C:1]#[CH:2])=[CH:4][CH:5]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11170993(4-Ethynylphenyl)methanol

Product 1

HCID 594357734-Ethynylbenzyl methanesulfonateYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-ethynylbenzyl alcohol (5.0 g, 37.8 mmol) in CH2Cl2 (50 mL) and triethylamine (Et3N) (14.4 mL, 104.0 mmol) was added mesyl chloride (8.04 mL, 104.0 mmol) at 0° C. and the reaction was allowed to warm to room temperature. Stirring continued for 2 h under argon during which TLC revealed a quantitative conversion into a higher Rf product. Ice cold water was added into the reaction mixture and extracted with Et2O (200 ml). The organic layer was washed with 1N HCL (70 ml), H2O (100 ml), aqueous NaHCO3 (70 ml), and finally H2O (100 ml); and then dried over Na2SO4. Solvent was evaporated off and dried in vacuo to give 7.0 g of compound 3 as brownish oil which was used without further purification.

Workup

  1. additionIce cold water was added into the reaction mixture
  2. extractionextracted with Et2O (200 ml)
  3. washThe organic layer was washed with 1N HCL (70 ml), H2O (100 ml), aqueous NaHCO3 (70 ml), and finally H2O (100 ml)
  4. dry with materialand then dried over Na2SO4
  5. customSolvent was evaporated off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-083069f06696482fb8af521dee74d4d7
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Linked notes

Loading…