tert-Butanol → N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

HRID 2376446ノート

反応式

HRID 2376446 の反応式
[C:1]([OH:5])([CH3:4])([CH3:3])C.[CH:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:19]3[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:22]([CH3:26])=C(C=C)[C:18]=3[O:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:8])[CH3:7].S([O-])([O-])=[O:37].[Na+].[Na+]>O.C1COCC1>[OH:5][CH:1]([C:4]1[C:18]2[O:17][CH2:16][CH:15]([C:12]3[CH:13]=[CH:14][C:9]([CH:6]([CH3:7])[CH3:8])=[CH:10][CH:11]=3)[C:19]=2[C:20]([CH3:35])=[C:21]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:32])([CH3:33])[CH3:31])[C:22]=1[CH3:26])[CH2:3][OH:37]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 23113980N-(3-(4-Isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

生成物 1

HCID 23114170N-(7-(1,2-Dihydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of AD-mix β (4.62 g) in a mixed solvent of water (15 mL), tert-butanol (15 mL) and THF (15 mL) was added with ice-cooling N-(3-(4-isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (670 mg, 1.65 mmol) obtained in Example 83 and the reaction mixture was stirred at 80° C. for 3 hours. To the reaction solution were added water and sodium sulfite and the resulting mixture was stirred at room temperature for 30 minutes. The product was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 558 mg (yield: 77%) of the title compound. Melting point: 159-161° C. (hexane-ethyl acetate).

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

出典と根拠

ORDレコード
ord-d7b63e8492cd431b9fd1eed5befc1fc2
出典データセット
uspto-grants-2008_12
特許番号
US07465815B2

反応ノート

読み込み中…