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

HRID 646013노트

반응식

HRID 646013 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[C:14]([C:15](OC)=[O:16])=[C:13]([CH:19]([CH3:21])[CH3:20])[O:12][N:11]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.O.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[C:14]([CH2:15][OH:16])=[C:13]([CH:19]([CH3:21])[CH3:20])[O:12][N:11]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 59264879Methyl 3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolecarboxylate

생성물 1

HCID 59264881[3-[(2,6-Dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methanol수율 99%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolecarboxylate (1.18 g, 3.6 mmol) (from multiple batches) in tetrahydrofuran (10 mL) was stirred at 0° C. as a 1.5 M solution of diisobutylaluminum hydride in toluene (3.7 mL, 5.6 mmol) was added. The solution was allowed to warm to room temperature and stir overnight. Methanol (0.27 mL) was added followed by water (2.7 mL) then 2 N sodium hydroxide (4 mL). The solution was filtered through celite. The filtrate was partitioned between ethyl acetate and water. An aqueous solution of Rochelle's salt was added. The organic layer was separated, dried with magnesium sulfate, concentrated and purified by chromatography (silica gel, 30% ethyl acetate in hexane) to provide the title compound (1.07 g, 99%). 1H NMR (DMSO-d6): δ 7.46 (d, J=8 Hz, 2H), 7.32 (t, J=8 Hz, 1H), 5.01 (t, J=5 Hz, 1H), 4.36 (d, J=5 Hz, 2H), 4.22 (s, 2H), 3.21 (septet, J=7 Hz, 1H) 1.20 (d, J=7 Hz, 6H). ESI-LCMS m/z 300 (M+H)+.

후처리

  1. additionwas added
  2. filtrationThe solution was filtered through celite
  3. customThe filtrate was partitioned between ethyl acetate and water
  4. additionAn aqueous solution of Rochelle's salt was added
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. custompurified by chromatography (silica gel, 30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-1843581e57604247be646456a39b7b5d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705028B2

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