Ammonium Chloride → 2-Cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17586ノート

反応式

HRID 17586 の反応式
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH:15]([CH2:20][CH:21]=[CH2:22])[C:16](OC)=[O:17])=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2].[Li+].[B-](CC)(CC)CC.[Cl-].[NH4+]>O1CCCC1>[CH:12]1([C:10]2[O:11][C:7]3[C:8](=[C:3]([C:1]#[N:2])[C:4]([CH3:29])=[C:5]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:6]=3[CH:15]([CH2:16][OH:17])[CH2:20][CH:21]=[CH2:22])[N:9]=2)[CH2:13][CH2:14]1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 23712863Lithium triethylborohydrideHCID 68584392Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate

生成物 1

HCID 685849552-Cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate (I-296) (100 mg, 0.26 mmol) was dissolved in tetrahydrofuran (2 ml), then under nitrogen atmosphere at −78° C., Super Hydride (1.0 M tetrahydrofuran solution) (570 μl, 0.52 mmol) was dropwise added. After stirring at the same temperature for 2 hours, aqueous saturated ammonium chloride solution was added, followed by further stirring at room, temperature for 10 minutes. The solution was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (88 mg, 95%) as a colorless gel.

後処理

  1. stirringby further stirring at room, temperature for 10 minutes
  2. extractionThe solution was extracted three times with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

出典と根拠

ORDレコード
ord-36bf63e59d384b628941c7ed23c0d940
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

読み込み中…