Toluene → [3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol

HRID 2423467노트

반응식

HRID 2423467 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([C:16](OC)=[O:17])=[C:14]([CH:20]([CH3:22])[CH3:21])[O:13][N:12]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1.C(OCC)(=O)C.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9][CH2:10][C:11]1[C:15]([CH2:16][OH:17])=[C:14]([CH:20]([CH3:22])[CH3:21])[O:13][N:12]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 59321546Methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate

생성물 1

HCID 59321503[3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol수율 93%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolecarboxylate (50 mg, 0.14 mmol) in tetrahydrofuran (0.5 mL) at 0° C. was slowly added a 1.5 M solution of diisobutylaluminum hydride in toluene (0.46 mL, 0.69 mmol). The solution was allowed to warm slowly to ambient temperature and stir overnight. The next day the solution was cooled to 0° C. and methanol (approximately 0.25 mL) was added followed by aqueous Rochelle's salt (approximately 3 mL). The mixture was diluted with ethyl acetate and allowed to warm to ambient temperature while stirring. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated to afford [3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methanol (43 mg, 93%). 1H-NMR (400 MHz, CDCl3) δ 7.35-7.16 (m, 3H), 4.60 (s, 2H), 4.10 (s, 2H), 3.17 (septet, J=8 Hz, 1H), 1.28 (d, J=6 Hz, 6H).

후처리

  1. temperatureThe next day the solution was cooled to 0° C.
  2. temperatureto warm to ambient temperature
  3. stirringwhile stirring
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-52b9f12008f045fdb20f330e0b6b94cf
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960552B2

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