Hexane → HCID 54717657, compound

HRID 1828644Notes

Reaction equation

HRID 1828644 reaction equation
C([O:5][C:6](=O)[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[S:17][CH2:18][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])CCC.[H-].[Na+].CCCCCC.C(OCC)(=O)C>CN(C=O)C.C(O)(=O)C>[CH2:22]([O:21][C:19]([C:18]1[S:17][C:8]2[CH:9]=[C:10]([O:15][CH3:16])[C:11]([O:13][CH3:14])=[CH:12][C:7]=2[C:6]=1[OH:5])=[O:20])[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21028584HCID 21028584, compound

Product 1

HCID 54717657HCID 54717657, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

19.22 g (50 mmol) XII were stirred for 3.5 h at room temperature with 2.75 g (63 mmol), 60%) NaH in 250 ml DMF. The mixture was then hydrolyzed with 50 ml saturated NH4Cl solution and the solvent was removed. The residue was taken up in 500 ml CHCl3, filtered, washed with water and dried over Na2SO4. Flash chromatography (250 g SiO2, n-hexane:ethyl acetate=5:1+1% acetic acid) gave 14.70 g (47 mmol, 95%) XIII.

Workup

  1. customhydrolyzed with 50 ml saturated NH4Cl solution and the solvent was removed
  2. filtrationfiltered
  3. washwashed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-6251f6a0b7c64ee38b695211254b7fd6
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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