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

HRID 132621

Reaktionsgleichung

Reaktionsgleichung von HRID 132621
[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]

Komponenten

6

Edukt 2

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

Produkt 1

HCID 865979554-Methyl-benzenesulfinic Acid ((2R,3R)-2,3-dimethyl-hexylidene)-amideAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76524Titanium tetraethoxideKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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%].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4e901b5c056e4996a8548ae3e5c5700d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388023B2

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