Water → Sarcophytol A

HRID 5671Notes

Reaction equation

HRID 5671 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-one

Product 1

HCID 5284454Sarcophytol AYield 90.3%

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 1M 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:-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-afd51883db244e12b7b5da102322d549
Source dataset
uspto-grants-1993_09
Patent number
US05245085

Reaction notes

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