Water → HCID 18408289, compound

HRID 992840Notes

Reaction equation

HRID 992840 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])[CH2:5]1.[H][H].O>CN(C)C=O>[CH2:7]([C:10]([CH:6]1[CH2:7][CH2:8][CH2:9][CH:4]([CH3:3])[CH2:5]1)([C:11]([O:13][CH3:14])=[O:12])[C:15]([O:17][CH3:18])=[O:16])[CH2:8][CH2:9][CH2:4][CH:5]=[CH2:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 18408270HCID 18408270, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18408289HCID 18408289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of sodium hydride (2.53 g, 0.06 mol) in anhydrous N,N-dimethylformamide (50 mL) was added dropwise dimethyl 2-(3-methylcyclohexyl)-malonate (14.46 g, 0.06 mol). After complete addition, the reaction was stirred until no more hydrogen gas was evolved. To the reaction was then added dropwise 1-bromo-6-hexene (10.33 g, 0.06 mol) followed by stirring. The progress of the reaction was followed by analytical chromatography using silica plates and ethyl acetate:hexanes (40:60). After complete reaction, water (20 mL) was added and most of the solvents removed under high vacuum. The remaining material was partitioned between water and ether and the ether layer washed twice with water. The ether solution was dried with MgSO4 and evaporated to give a thick yellow oil. The product was then distilled at 127-134° C. and 0.4 mm pressure to give clear oil.

Workup

  1. additionAfter complete addition
  2. additionwas added and most of the solvents
  3. customremoved under high vacuum
  4. customThe remaining material was partitioned between water and ether
  5. washthe ether layer washed twice with water
  6. dry with materialThe ether solution was dried with MgSO4
  7. customevaporated
  8. customto give a thick yellow oil
  9. distillationThe product was then distilled at 127-134° C.
  10. custom0.4 mm pressure to give clear oil

Sources & evidence

ORD record
ord-5854e44b6bf2413a94365480d043c691
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

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