Water → Sarcophytol A

HRID 1886201Notes

Reaction equation

HRID 1886201 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 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The ketone compound shown above [2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one] (137 mg, 0.48 mmol) was dissolved in dry toluene (2.5 ml). To the solution was added with stirring on a cold bath at -70° C. under argon atmosphere 1M solution of diisobutylaluminum hydride in toluene (0.6 ml). Disappearance of the starting material was confirmed 1 hour later, and the mixture was mixed with 0.25 ml of water. The bath was removed, and the mixture was stirred well, dried over anhydrous magnesium sulfate, stirred, and filtered. The filtrate was concentrated. The residue was chromatographed on a silica gel column (Eluent: n-hexane:ethyl acetate=12:1) to give sarcophytol A (125 mg, 88%).

Workup

  1. additionTo the solution was added
  2. customThe bath was removed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. stirringstirred
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customThe residue was chromatographed on a silica gel column (Eluent: n-hexane:ethyl acetate=12:1)

Sources & evidence

ORD record
ord-9a1cfda5cf3b42d08bb47da583d108fa
Source dataset
uspto-grants-1992_09
Patent number
US05149843

Reaction notes

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