Sodium hydride → HCID 178468870, compound

HRID 1035708Notes

Reaction equation

HRID 1035708 reaction equation
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH:19]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=O.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[C:13]([O:12][C:10](/[CH:9]=[CH:19]/[C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:36][CH:37]=2)[CH2:23][CH2:22]1)=[O:11])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 2773685tert-Butyl diethylphosphonoacetateHCID 178468872HCID 178468872, compound

Product 1

HCID 178468870HCID 178468870, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.682 g of tert-butyl diethylphosphonoacetate (2.7 mmol, 1.1 eq.) is placed in 5 mL of DMF at 4° C. with stirring, 0.065 g of sodium hydride (2.7 mmol, 1.1 eq.) is added. After stirring for 1 hour, 0.64 g of ethyl trans-4-(4-formylcyclohexyl)benzoate (2.46 mmol, 1 eq.) dissolved in 5 mL of DMF is added dropwise. After stirring for 18 hours, 10% potassium hydrogen sulfate solution is added. The reaction medium is extracted twice with ethyl acetate. The organic phases are combined, washed twice with water, washed with brine, dried over sodium sulfate and evaporated. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%. 0.71 g of ethyl trans-4-[4-((E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoate is obtained.

Workup

  1. stirringAfter stirring for 1 hour
  2. additionis added dropwise
  3. stirringAfter stirring for 18 hours
  4. extractionThe reaction medium is extracted twice with ethyl acetate
  5. washwashed twice with water
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 20%

Sources & evidence

ORD record
ord-737ff7aed4df4910bdf67333ac419e00
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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