tert-Butylsulfinamide, (R)-(+)- → (NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

HRID 1361167ノート

反応式

HRID 1361167 の反応式
[CH3:1][S:2]([C:5]1[O:9][C:8]([C:10](=O)[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[O:9][C:8](/[C:10](=[N:20]/[S@@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

参加物

7

反応物 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 592781411-(5-Methanesulfonyl-furan-2-yl)-propan-1-one

生成物 1

HCID 59278140(NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

試薬・触媒・溶媒 4

HCID 11026Titanium isopropoxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(5-methanesulfonyl-furan-2-yl)-propan-1-one (1.1 g, 5.5 mmol) in THF (30 mL) was added (R)-(+)-2-methyl-2-propanesulfinamide (0.750 g, 6.06 mmol) and titanium (IV) isopropoxide (6 mL, 25 mmol) and the mixture was warmed at reflux. After 18 hours, the mixture was cooled to room temperature, and diluted with diethyl ether (100 mL) and water (6 mL). The mixture was stirred for 10 minutes, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-80% EtOAc-hexanes to afford (R)-2-methyl-propane-2-sulfinic acid[1-(5-methanesulfonyl-furan-2-yl)-prop-(E)-ylidene]-amide.

後処理

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of 0-80% EtOAc-hexanes

出典と根拠

ORDレコード
ord-20925c42e2b94c59bf47461a05c8c1bb
出典データセット
uspto-grants-2011_02
特許番号
US07879873B2

反応ノート

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