Barbituric Acid → HCID 178451368, compound

HRID 1035722Notes

Reaction equation

HRID 1035722 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C=C.N1C(=O)CC(=O)NC1=O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6211Barbituric AcidHCID 178458392HCID 178458392, compound

Product 1

HCID 178451368HCID 178451368, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.6 g of tert-butyl trans-[4-(4-allyloxyphenyl)cyclohexyloxy]acetate are dissolved in 70 mL of dichloromethane, to which are added with stirring 4.87 g of barbituric acid (31.17 mmol, 3 eq.) and then 1.20 g of tetrakis(triphenylphosphine)palladium (1.04 mmol, 0.1 eq.). The reaction medium is refluxed for 3 hours. After 16 hours at room temperature, the reaction medium is diluted with dichloromethane and washed with brine. The aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on silica gel, eluting with a gradient of ethyl acetate in heptane ranging from 2% to 20%. 3.2 g of tert-butyl trans-[4-(4-hydroxyphenyl)cyclohexyloxy]acetate are obtained.

Workup

  1. additionare added
  2. temperatureThe reaction medium is refluxed for 3 hours
  3. washwashed with brine
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is chromatographed on silica gel
  10. washeluting with a gradient of ethyl acetate in heptane ranging from 2% to 20%

Sources & evidence

ORD record
ord-13f07f22083849529e93f5f8336217fa
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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