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

HRID 646013ノート

反応式

HRID 646013 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-1843581e57604247be646456a39b7b5d
出典データセット
uspto-grants-2010_04
特許番号
US07705028B2

反応ノート

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