Water → Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester

HRID 751207Notes

Reaction equation

HRID 751207 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:6][CH:5]=1.CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>ClCCl>[F:1][C:2]([F:16])([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][O:15][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688226904-Pentyn-1-ol, 5-[4-(trifluoromethoxy)phenyl]-

Product 1

HCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (2.02 g, 8.3 mmol; example 1 a]) and Et3N (1.73 ml, 12.4 mmol) in dichloromethane (100 ml) was added methanesulfonyl chloride (0.67 ml, 8.7 mmol) within 15 min keeping the temperature at 0-10° C. The reaction mixture was stirred at RT for 1 h 15 min. Water was added and after 5 min, the reaction was partitioned between ether and water. The aqueous layer was extracted again with ether (2×), the organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and concentrated to yield 2.5 g (7.7 mmol, 93%) of the title compound as light brown oil.

Workup

  1. customat 0-10° C
  2. customthe reaction was partitioned between ether and water
  3. extractionThe aqueous layer was extracted again with ether (2×)
  4. washthe organic phases were washed with aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fb6dae916eb4e7495b65305fc872fd2
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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