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

HRID 132621

반응식

HRID 132621 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 76524Titanium tetraethoxide촉매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

실험 절차

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%].

후처리

  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

출처 및 근거

ORD 기록
ord-4e901b5c056e4996a8548ae3e5c5700d
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388023B2

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