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

HRID 852355

反応式

HRID 852355 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 11616756Methanesulfonic acid 5-(4-trifluoromethoxy-phenyl)-pent-4-ynyl ester収率 93.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice-cooled solution of 2.02 g (8.3 mmol) of 5-(4-trifluoromethoxy-phenyl)-pent-4-yn-1-ol and 1.73 ml (12.4 mmol) of Et3N in 100 ml of dichloromethane were added 0.67 ml (8.7 mmol) of methanesulfonyl chloride under stirring 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 then partitioned between ether and water. The water was extracted again with ether (two times), the organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and concentrated to yield 2.50 g of the title compound as light brown oil.

後処理

  1. customat 0-10° C
  2. stirringThe reaction mixture was stirred at RT for 1 h 15 min
  3. customthe reaction was then partitioned between ether and water
  4. extractionThe water was extracted again with ether (two times)
  5. washthe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0da8e9772ec7451db539bfe6cbdaf814
出典データセット
uspto-grants-2007_08
特許番号
US07253192B2

関連ノート

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