Hydrochloric Acid → HCID 18676124, compound

HRID 1635480Notes

Reaction equation

HRID 1635480 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[C:13]1([C:19]2[C:20]3[CH:32]=[CH:31][CH:30]=[CH:29][C:21]=3[O:22][CH2:23][C:24]=2[CH2:25][C:26]([OH:28])=[O:27])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.BrCCCC.Cl>O1CCCC1.CCCCCC.CCCCC.O>[C:13]1([C:19]2[C:20]3[CH:32]=[CH:31][CH:30]=[CH:29][C:21]=3[O:22][CH2:23][C:24]=2[CH:25]([CH2:8][CH2:9][CH2:10][CH3:11])[C:26]([OH:28])=[O:27])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 8002Butyl bromideHCID 10999979HCID 10999979, compoundHCID 178418339Butyllithium

Product 1

HCID 18676124HCID 18676124, compoundYield 52.8%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

3.1 ml (22 mmol) of diisopropylamine in solution in 20 ml of tetrahydrofuran are placed in a 250-ml reactor protected from moisture, and then 13.75 ml (22 mmol) of n-butyllithium in hexane (1.6 M) are added dropwise to this solution kept at 0° C. After stirring the reaction medium for 15 minutes at 0° C., 2.66 g (10 mmol) of 2-(4-phenyl-2H-3-benzo[b]pyranyl)acetic acid are added dropwise to this solution kept at 0° C. The reaction medium is stirred for 2 hours at 0° C. and then 1.18 ml (11 mmol) of 1-bromobutane are poured into this solution kept at this temperature of 0° C. The reaction mixture is stirred for 72 hours at room temperature. After addition of water and hydrochloric acid (2 M), the reaction mixture is extracted with diethyl ether. The organic phase, after washing with water, is dried and then evaporated off. The oil obtained is chromatographed on a silica gel (eluent: methylene chloride). After evaporation of the solvent, the crystals obtained are dispersed in pentane and then drained. 1.7 g of the expected compound are thus obtained, that is to say a yield of 52.8%. This compound has a melting point of between 117 and 119° C.

Workup

  1. additionare added dropwise to this solution
  2. customkept at 0° C
  3. customkept at 0° C
  4. stirringThe reaction medium is stirred for 2 hours at 0° C.
  5. customkept at this temperature of 0° C
  6. stirringThe reaction mixture is stirred for 72 hours at room temperature
  7. extractionthe reaction mixture is extracted with diethyl ether
  8. washThe organic phase, after washing with water
  9. customis dried
  10. customevaporated off
  11. customThe oil obtained
  12. customis chromatographed on a silica gel (eluent: methylene chloride)
  13. customAfter evaporation of the solvent
  14. customthe crystals obtained

Sources & evidence

ORD record
ord-b48d8c2cbe984af1a3db40d07b959a3c
Source dataset
uspto-grants-2003_01
Patent number
US06509362B2

Reaction notes

Loading…