Diisobutylaluminum hydride → HCID 22226108、化合物

HRID 1883268ノート

反応式

HRID 1883268 の反応式
C(O[C:4](=[O:27])/[C:5](/[F:26])=[C:6](\[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)/[CH3:7])C.[CH3:28]C(C[AlH]CC(C)C)C>C1COCC1>[F:26]/[C:5](=[C:6](/[C:8]1[C:17]([O:18][CH2:19][CH2:20][CH3:21])=[CH:16][C:15]2[C:14]([CH3:23])([CH3:22])[CH2:13][CH2:12][C:11]([CH3:25])([CH3:24])[C:10]=2[CH:9]=1)\[CH2:7][CH3:28])/[CH2:4][OH:27]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 20740816(E)-2-Fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester

生成物 1

HCID 22226108HCID 22226108、化合物収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of(E)-2-fluoro-3-(5,5,8,8-tetramethyl-3-propoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester (Intermediate 6, 2.2 g, 5.85 mmol) in THF (50 mL) at −78° C. was added DIBAL-H (23.4 mL, 1.0 M in CH2Cl2, 23.4 mmol) over 10 min. After stirring at −78° C. for 3 h, the reaction was quenched with aqueous NH4Cl followed by 1M HCl and was extracted with Et2O (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane) to give the title compound (1.02 g, 45% over 2 steps).

後処理

  1. customthe reaction was quenched with aqueous NH4Cl
  2. extractionwas extracted with Et2O (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-1b4f710c95f04873b3cbff6dbf6ca583
出典データセット
uspto-grants-2004_07
特許番号
US06759547B1

反応ノート

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