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

HRID 2423467ノート

反応式

HRID 2423467 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-52b9f12008f045fdb20f330e0b6b94cf
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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