Water → Sarcophytol A

HRID 892646Notes

Reaction equation

HRID 892646 reaction equation
[CH3:1][CH:2]([C:4]1[C:5](=[O:21])[CH2:6][C:7]([CH3:20])=[CH:8][CH2:9][CH2:10][C:11]([CH3:19])=[CH:12][CH2:13][CH2:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[CH3:19][C:11]1=[CH:12][CH2:13][CH2:14][C:15]([CH3:18])=[CH:16][CH:17]=[C:4]([CH:2]([CH3:1])[CH3:3])[C@@H:5]([OH:21])[CH2:6][C:7]([CH3:20])=[CH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 570081642-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one

Product 1

HCID 5284454Sarcophytol AYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Under argon atmosphere, to a solution of the ketone, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-on (137 mg, 0.48 mmol) prepared in Reference Example 8 in dry toluene (25 ml) is dropwise added a 1 M solution of diisobutylaluminum hydride in toluene (0.6 ml) while stirring on a refrigerant bath at -70° C. After 1 hour, disappearance of the starting compound is confirmed. To the mixture is added water (0.25 ml) and the mixture is stirred enough after removing the bath. The mixture is dried over anhydrous magnesium sulfate, stirred, filtered and concentrated. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =12:1) to give the desired Sarcophytol A (125 mg, 88%).

Workup

  1. stirringthe mixture is stirred enough
  2. customafter removing the bath
  3. dry with materialThe mixture is dried over anhydrous magnesium sulfate
  4. stirringstirred
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =12:1)

Sources & evidence

ORD record
ord-98864c7e6ea2489a92244cefa9b56bae
Source dataset
uspto-grants-1992_06
Patent number
US05118827

Reaction notes

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