Acetonitrile → HCID 58079491, compound

HRID 444989Notes

Reaction equation

HRID 444989 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)([CH3:4])([CH3:3])[CH3:2].[CH3:23][O:24][C:25](=[O:40])[C:26]1[CH:38]=[CH:37][C:36]([OH:39])=[C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:27]=1.C([O-])([O-])=O.[K+].[K+].C(#N)C>CCCCCCC.CCOC(C)=O>[CH3:23][O:24][C:25](=[O:40])[C:26]1[CH:38]=[CH:37][C:36]([O:39][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])=[C:28]([C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH:27]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 23062509HCID 23062509, compoundHCID 58079429HCID 58079429, compound

Product 1

HCID 58079491HCID 58079491, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

15-Bromo-pentadecanoic acid tert-butyl ester (598 mg, 1.59 mmol), 4-hydroxy isophthalic acid 3-tert-butyl ester 1-methyl ester (400 mg, 1.59 mmol) and K2CO3 (329 mg, 2.38 mmol) were placed in a flask with acetonitrile (25 ml) and refluxed under N2. The reaction was followed via TLC (4:1 heptane/AcOEt). After 13 h the sample was concentrated under vacuum to near dryness. AcOEt (50 ml) and water (25 ml) were added to the residue. The phases were separated and the organic phase was washed with water and brine (25 ml each), dried over MgSO4 and concentrated to yield an oil (841 mg, 97%).

Workup

  1. temperaturerefluxed under N2
  2. concentrationAfter 13 h the sample was concentrated under vacuum
  3. additionAcOEt (50 ml) and water (25 ml) were added to the residue
  4. customThe phases were separated
  5. washthe organic phase was washed with water and brine (25 ml each)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5f9ad986631c45cdbf6d5fea2d3431d0
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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