Potassium Carbonate → HCID 18414624, compound

HRID 843626Notes

Reaction equation

HRID 843626 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:16])[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=1)[CH:31]([OH:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[O:16][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=1)[CH:31]([OH:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18414620HCID 18414620, compoundHCID 18414623HCID 18414623, compound

Product 1

HCID 18414624HCID 18414624, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-propyl-4-cyclohexylphenol (0.9 g) (as prepared in Step A), potassium carbonate (0.69 g) and ethyl 3-(3-bromopropoxy)mandelate (1.18 g) in DMF (30 mL) was stirred at 40° C. for 30 h. The reaction mixture was partitioned between ethyl acetate and 1.0 N HCl. The organic layer was washed twice with water, once with brine and then dried over sodium sulfate. The organic layer was then filtered and the solvent remove in vacuo. The resulting oil was chromatographed on silica gel, using ethyl acetate/hexane to yield the titled compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1.0 N HCl
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was then filtered
  5. customthe solvent remove in vacuo
  6. customThe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-71496a6517ba41c5a303691f088125ff
Source dataset
uspto-grants-2002_04
Patent number
US06380191B1

Reaction notes

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