(S)-4-methylbenzenesulfinamide → 4-Methyl-benzenesulfinic Acid ((2R,3R)-2,3-dimethyl-hexylidene)-amide

HRID 132621

反応式

HRID 132621 の反応式
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([S@@:7]([NH2:9])=[O:8])=[CH:3][CH:2]=1.[CH3:11][C@H:12]([C@H:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:13]=O>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH3:11][C@H:12]([C@H:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:13]=[N:9][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)=[O:8]

参加物

6

反応物 2

HCID 11116285(S)-4-methylbenzenesulfinamideHCID 57444839(2R,3R)-2,3-Dimethyl-hexanal

生成物 1

HCID 865979554-Methyl-benzenesulfinic Acid ((2R,3R)-2,3-dimethyl-hexylidene)-amide収率 51.7%

試薬・触媒・溶媒 3

HCID 76524Titanium tetraethoxide触媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Titanium(IV) ethoxide (5.16 g, 22.6 mmol) and (S)-(+)-p-toluenesulfinamide (7.02 g, 45.2 mmol) were added to (2R,3R)-2,3-dimethyl-hexanal (2.9 g, 22.6 mmol) in dry THF (30 mL). The resulting mixture was stirred at room temperature for 18 hours and poured into a brine solution (40 mL). The slurry was rapidly stirred for 10 minutes and filtered. The filtrate was extracted into ethyl acetate, washed with brine and dried over MgSO4. The solvent was evaporated and the residue was filtered through a silica plug, eluting with 50/50 solution of hexane/ethyl acetate to afford the titled compound (3.1 g, 51.6% yield) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 0.8 (m, 6H) 1.1 (m, 4H) 1.3 (m, 3H) 1.7 (m, 1H) 2.4 (s, 3H) 2.5 (m, 1H) 7.3 (d, J=8.3 Hz, 2H) 7.5 (d, J=8.1 Hz, 2H) 8.1 (d, J=5.4 Hz, 1H). MS, m/z (relative intensity): 266 [M+1H, 100%].

後処理

  1. stirringThe slurry was rapidly stirred for 10 minutes
  2. filtrationfiltered
  3. extractionThe filtrate was extracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated
  7. filtrationthe residue was filtered through a silica plug
  8. washeluting with 50/50 solution of hexane/ethyl acetate

出典と根拠

ORDレコード
ord-4e901b5c056e4996a8548ae3e5c5700d
出典データセット
uspto-grants-2008_06
特許番号
US07388023B2

関連ノート

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