Potassium Carbonate → HCID 66724581, compound

HRID 1425653Notes

Reaction equation

HRID 1425653 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:15][O:16][C:17](=[O:28])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:17]([O:16][CH3:15])=[O:28])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 554079Methyl 10-bromodecanoate

Product 1

HCID 66724581HCID 66724581, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-benzoic acid tert-butyl ester (500 mg, 2.57 mmol) and 10-bromodecanoic acid methyl ester (683 mg, 2.57 mmol) were dissolved in acetonitrile, and K2CO3 (712 mg, 5.15 mmol) was added. The mixture was refluxed under nitrogen for 16 h, and cooled to rt. The solids were filtered off, and the filtrate concentrated under vacuum. The resulting residue was dissolved in AcOEt (50 ml) and water (25 mL). The phases were separated and the organic phase was dried over MgSO4 and concentrated to yield a colorless oil (874 mg, 90% yield).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 16 h
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate concentrated under vacuum
  4. dissolutionThe resulting residue was dissolved in AcOEt (50 ml)
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc09fc7725741e083a39c8cacc67ea1
Source dataset
uspto-grants-2015_01
Patent number
US08933021B2

Reaction notes

Loading…