Hexane → HCID 57144497, compound

HRID 863338Notes

Reaction equation

HRID 863338 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[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])[CH:15]=[CH:16][C:17](OC)=[O:18].CCCCCC.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:23][Si:2]([CH3:1])([CH3:22])[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])[CH:15]=[CH:16][CH2:17][OH:18]

Participants

5

Reactant 3

HCID 8058HexaneHCID 21225700Diisobutylaluminumhydride2×HCID 56995888HCID 56995888, compound

Product 1

HCID 57144497HCID 57144497, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-95 °C

Procedure

A 3.66 g amount of methyl(4R)-4-[(1R,7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-yl]-2-pentenoate was placed in a 500 ml eggplant-shaped flask, and 100 ml of hexane and 40 ml of toluene were then added to dissolve it. The solution was cooled to -95° C., then 12.2 ml of diisobutylaluminum hydride was slowly added and the solution stirred at the same temperature for 1 hour. Next, a further 24 ml of diisobutylaluminum hydride was added, followed by stirring for 2 hours. The consumption of the material was confirmed by thin layer chromatography, then the excess reducing agent was broken down by methanol and a saturated aqueous solution of sodium sulfate and then 300 ml of ethyl acetate and 80 ml of a saturated aqueous solution of ammonia chloride were added for separation. Extraction was performed from the aqueous layer by 100 ml of ethyl acetate, then the organic layer was washed with saturated saline and was dried by anhydrous magnesium sulfate. The desiccant was filtered out, then the filtrate was concentrated under reduced pressure to obtain a crude product in an amount of 3.61 g. This was purified by a silica column (hexane/ethyl acetate=19/1 to 4/1) to obtain (4R)-4-[(1R, 7aR)-octahydro-4-trimethylsilyloxy-7a-methyl-1H-inden-1-y l]-2-penten-1-ol in an amount of 3.31 g (98%).

Workup

  1. dissolutionto dissolve it
  2. stirringby stirring for 2 hours
  3. customThe consumption of the material
  4. additiona saturated aqueous solution of sodium sulfate and then 300 ml of ethyl acetate and 80 ml of a saturated aqueous solution of ammonia chloride were added for separation
  5. extractionExtraction
  6. washthe organic layer was washed with saturated saline
  7. dry with materialwas dried by anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered out
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto obtain a crude product in an amount of 3.61 g
  11. customThis was purified by a silica column (hexane/ethyl acetate=19/1 to 4/1)

Sources & evidence

ORD record
ord-be94e653bfc844ddb9463d7b23f7c8f7
Source dataset
uspto-grants-1998_02
Patent number
US05719297

Reaction notes

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