Hexane → (4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-pentanal

HRID 1603281

반응식

HRID 1603281 반응식
[CH3:1][Si:2]([CH3:25])([CH3:24])[O:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH2:21]CC)[CH2:15][CH2:16][C:17](OC)=[O:18].CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].N>CCOCC.CO>[CH3:25][Si:2]([CH3:1])([CH3:24])[O:3][CH:4]1[CH2:12][CH2:11][CH2:10][C@@:9]2([CH3:13])[CH:5]1[CH2:6][CH2:7][C@@H:8]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH:17]=[O:18]

참가 물질

7

반응물 4

HCID 8058Hexane2회HCID 20976574Ammonia chlorideHCID 21225700DiisobutylaluminumhydrideHCID 22882749methyl(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-heptanoate

생성물 1

HCID 57264692(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-pentanal수율 92%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

반응 조건

온도
-95 °C

실험 절차

A 3.79 g amount of the compound (4-6), methyl(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-heptanoate was taken in a 300 ml eggplant-shaped flask, 100 ml of hexane was added, and the solution was stirred and cooled to -95° C. Thereafter 12.3 ml of a hexane solution (0.93 mol/liter) of diisobutylaluminum hydride was added and the solution stirred for 1 hour. A 100 ml amount of methanol was used to break down the excess reducing agent, then 30 ml of a saturated aqueous solution of ammonia chloride and 50 ml of ether were added and the solution was stirred at room temperature for 1 hour. The insolubles were removed by filtration by Celite, then the solution was separated and the aqueous layer was extracted by ether. The organic layer was washed two times by saturated saline in an amount of 50 ml, then was dried over anhydrous magnesium sulfate. The desiccant was filtered out, then the solvent was distilled off under reduced pressure to obtain a crude product in an amount of 4.07 g. This was purified by a silica gel column (Merck gel: 300 g, hexane/ethyl acetate=50/1) to obtain the desired product (4-7), (4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-pentanal in an amount of 3.17 g (yield 92%).

후처리

  1. stirringthe solution stirred for 1 hour
  2. stirringthe solution was stirred at room temperature for 1 hour
  3. customThe insolubles were removed by filtration by Celite
  4. customthe solution was separated
  5. extractionthe aqueous layer was extracted by ether
  6. washThe organic layer was washed two times by saturated saline in an amount of 50 ml
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered out
  9. distillationthe solvent was distilled off under reduced pressure
  10. customto obtain a crude product in an amount of 4.07 g
  11. customThis was purified by a silica gel column (Merck gel: 300 g, hexane/ethyl acetate=50/1)

출처 및 근거

ORD 기록
ord-08e66fce29ab4a4fa5f5354166e04707
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986112

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