Water → Sarcophytol A

HRID 1609350Notes

Reaction equation

HRID 1609350 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.CCCCCC.C(OCC)(=O)C>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

6

Reactant 4

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 21226206Ethyl acetate hexaneHCID 570081642-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one2×

Product 1

HCID 5284454Sarcophytol AYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To the above ketone compound, 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraen-1-one (137 mg, 0.48 mmol) in dry toluene (2.5 ml) was dropwise added with stirring on a cooling bath at -70° C. a solution of 1 M diisobutyl aluminium hydride in toluene (0.6 ml). One hour later, disappearance of the starting material was confirmed. After addition of water (0.25 ml) and removal of the cooling bath, the reaction mixture was stirred, followed by drying over MgSO4, filtration, and concentration to give a residue, which was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=12:1) to obtain the aimed sarcophytol A (125 mg, 88%).

Workup

  1. customOne hour
  2. dry with materialby drying over MgSO4, filtration, and concentration
  3. customto give a residue, which

Sources & evidence

ORD record
ord-a67b036c2c0745fc8a61a37a27a94267
Source dataset
uspto-grants-1995_03
Patent number
US05399724

Reaction notes

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