Toluene → HCID 86618041, compound

HRID 1160587Notes

Reaction equation

HRID 1160587 reaction equation
C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.C[O:19][C:20](=O)/[CH:21]=[C:22](\[CH3:39])/[CH2:23]/[CH:24]=[CH:25]/[C@H:26]([CH3:38])[C@@H:27]([O:30][Si:31]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:32][CH3:33])[CH2:28][CH3:29].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH3:39]/[C:22](/[CH2:23]/[CH:24]=[CH:25]/[C@H:26]([CH3:38])[C@@H:27]([O:30][Si:31]([CH2:34][CH3:35])([CH2:36][CH3:37])[CH2:32][CH3:33])[CH2:28][CH3:29])=[CH:21]\[CH2:20][OH:19]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700DiisobutylaluminumhydrideHCID 86618042HCID 86618042, compound

Product 1

HCID 86618041HCID 86618041, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1M toluene solution (1.76 ml, 1.76 mmol) of diisobutylaluminum hydride was added dropwise to a toluene (6 ml) solution of methyl-(2E,5E,7S,8S)-3,7-dimethyl-8-[(triethylsilyl)oxy]deca-2,5-dienoate (0.22 g, 0.64 mmol) at −78° C. and the reaction solution was stirred at the same temperature for 30 minutes. The reaction solution was diluted with diethyl ether, followed by addition of a saturated potassium sodium tartrate tetrahydrate aqueous solution (1.0 ml) and was warmed to room temperature and stirred for two hours. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=8:1) to obtain the title compound (150 mg) as a colorless oil.

Workup

  1. stirringstirred for two hours
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. filtrationthe drying agent was filtered off
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=8:1)

Sources & evidence

ORD record
ord-30f69a32d22240c0b64012e46382f55c
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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