Citric Acid → HCID 66988303, compound

HRID 540395Notes

Reaction equation

HRID 540395 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[Br-].C(CCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.[C:38]([N:57]1[CH:61]=[C:60]([CH:62]=O)[N:59]=[CH:58]1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[C:64]([OH:76])(=[O:75])[CH2:65][C:66]([CH2:71][C:72](O)=O)(C(O)=O)O>C1COCC1>[C:38]([N:57]1[CH:61]=[C:60]([CH:62]=[CH:72][CH2:71][CH2:66][CH2:65][C:64]([OH:76])=[O:75])[N:59]=[CH:58]1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 66988303HCID 66988303, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-75 °C

Procedure

13.5 ml (14.3 mmol) of a solution of lithium hexamethyldisilazane at 1.06 M in THF are added to 3.27 g (7.38 mmol) of (4-carboxybutyl)triphenyl-phosphonium bromide in suspension in 45 ml of THF cooled to −75° C. The reaction medium is stirred at −75° C. for 20 minutes and then at 0° C. for 15 minutes. After a return to −75° C., 1.50 g (4.43 mmol) of 1-trit-yl-1H-imidazole-4-carbaldehyde in suspension in 15 ml of THF are introduced. After a return to ambient temperature, the reaction medium is stirred for 20 hours and then at 90° C. with microwave-heating for 5 minutes. The reaction medium is filtered and concentrated in a rotary evaporator and then taken up in 1/1 heptane/EtOAc. The organic phase is washed with a saturated aqueous solution of NaHCO3. The aqueous phase obtained is acidified to pH=5 with an aqueous solution of citric acid at 5% and then extracted with a 1/1 heptane/EtOAc mixture. The organic phase is dried over MgSO4, filtered and concentrated in a rotary evaporator. 0.58 g of 6-(1-trityl-1H-imidazol-4-yl)hex-5-enoic acid in the form of a beige powder are obtained with a yield of 31%.

Workup

  1. waitat 0° C. for 15 minutes
  2. stirringAfter a return to ambient temperature, the reaction medium is stirred for 20 hours
  3. temperatureat 90° C. with microwave-heating for 5 minutes
  4. filtrationThe reaction medium is filtered
  5. concentrationconcentrated in a rotary evaporator
  6. washThe organic phase is washed with a saturated aqueous solution of NaHCO3
  7. customThe aqueous phase obtained
  8. extractionextracted with a 1/1 heptane/EtOAc mixture
  9. dry with materialThe organic phase is dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-0f6d8efa2f3d49749b7ff1d78e63e279
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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