Hydrochloric Acid → HCID 18971235, compound

HRID 2395235Notes

Reaction equation

HRID 2395235 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C([NH:9][CH:10](C)C)(C)C.[CH:13]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.ClC(OCC)=[O:23].Cl.O1[CH2:32][CH2:31][CH2:30]C1>>[CH2:1]([NH:9][C:10]([C:13]1([C:18]([OH:20])=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:23])[C:2]1[CH:30]=[CH:31][CH:32]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 18840Cyclopentanecarboxylic acidHCID 178418339Butyllithium

Product 1

HCID 18971235HCID 18971235, compound

Conditions

Temperature
-70 °C

Procedure

480 mmol of butyllithium are added to 480 mmol of diisopropylamine in 600 ml of anhydrous tetrahydrofuran (THF), under argon, at -70° C. After stirring for 15 minutes at -70° C., 240 mmol of cyclopentanecarboxylic acid are added dropwise. After warming to room temperature, the mixture is heated for one hour at 50° C. The reaction medium is then cooled to -70° C. and 260 mmol of ethyl chloroformate are added. The solution is stirred for 20 minutes and then poured into ice-water. The medium is acidified with concentrated hydrochloric acid and then extracted with dichloromethane. The organic phase is then washed with water to neutral pH and then with saturated sodium chloride solution. After drying and evaporation, the expected product is obtained in the form of an oil.

Workup

  1. temperatureAfter warming to room temperature
  2. temperaturethe mixture is heated for one hour at 50° C
  3. temperatureThe reaction medium is then cooled to -70° C.
  4. stirringThe solution is stirred for 20 minutes
  5. extractionextracted with dichloromethane
  6. washThe organic phase is then washed with water to neutral pH
  7. customAfter drying
  8. customevaporation

Sources & evidence

ORD record
ord-a40983275556495bad7fa180049b1ab2
Source dataset
uspto-grants-1998_09
Patent number
US05814622

Reaction notes

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