Diisobutylaluminum hydride → HCID 22226108, 화합물

HRID 1883268노트

반응식

HRID 1883268 반응식
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]

참가 물질

4

반응물 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

생성물 1

HCID 22226108HCID 22226108, 화합물수율 45%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b4f710c95f04873b3cbff6dbf6ca583
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759547B1

반응 노트

불러오는 중…