Acetonitrile → HCID 58079491, compound

HRID 562529Notes

Reaction equation

HRID 562529 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-73f4cdf9bcdd48268188b0ef2f94e35c
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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