Hexane → HCID 54260529, compound

HRID 2260445Notes

Reaction equation

HRID 2260445 reaction equation
[H-].[Na+].CCCCCC.[CH3:9][C:10]([C:13]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[CH:22][C:14]=1[O:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[OH:21])([CH3:12])[CH3:11].Cl[CH2:31][C:32]([O-:34])=[O:33].[Na+]>CS(C)=O>[CH3:12][C:10]([C:13]1[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[CH:22][C:14]=1[O:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[O:21][CH2:31][C:32]([OH:34])=[O:33])([CH3:9])[CH3:11]

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 23665759Sodium chloroacetateHCID 54360737HCID 54360737, compound

Product 1

HCID 54260529HCID 54260529, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To 103 mg of 60% sodium hydride, prewashed with hexane, in 10 ml of dimethyl sulfoxide was added 500 mg of the title product of Example 100. The mixture was stirred at 40° C. until gas evolution ceased, and then 290 mg of sodium chloroacetate was added, the resulting mixture stirred at room temperature overnight and then at 80° for 1 hour. After cooling, the mixture was partitioned between diethyl ether and dilute aqueous hydrochloric acid, the aqueous layer further extracted with ether, the combined organic extracts washed with several portions of water and then brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using 30% ethyl acetate-2% acetic acid-68% hexane gave the title compound (155 mg) as a pure white crystalline solid, DSC 96.5° C.

Workup

  1. stirringthe resulting mixture stirred at room temperature overnight
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between diethyl ether and dilute aqueous hydrochloric acid
  4. extractionthe aqueous layer further extracted with ether
  5. washthe combined organic extracts washed with several portions of water
  6. dry with materialbrine, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-44c616c96f9e41daa7411fceaeceaaec
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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