Hydrochloric Acid → HCID 19801164, compound

HRID 1646599Notes

Reaction equation

HRID 1646599 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.Cl.C([O:10][CH:11]([CH3:13])[CH3:12])(C)C.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH2:16]([C:17]1[CH:3]=[CH:2][CH:1]=[C:19]2[C:18]=1[CH2:13][CH:11]([OH:10])[CH2:12]2)[CH:15]=[CH2:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 19801164HCID 19801164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-65 °C

Procedure

5.50 g of product obtained above is agitated in 30 ml of anhydrous tetrahydrofuran, cooled to -65° C. and 15.7 ml of a 1.6M butyllithium solution in hexane is introduced over half an hour, followed by agitation for one and a half hours at -65° C. 2.21 g of dry cuprous chloride is added in one lot and the suspension obtained is left for half an hour at -65° C. The latter is added in small amounts and under inert atmosphere to a solution, cooled to -70° C., of 4.20 ml of bromoallyl in 21 ml of tetrahydrofuran and the mixture is left for one hour at -70° C., -65° C. The reaction mixture is poured into 200 ml of 2N hydrochloric acid containing ice and 100 ml of isopropyl ether, then agitated for one hour at ambient temperature. The insoluble part is filtered off, decanted, the organic phase is washed with water, and the aqueous phases are extracted with isopropyl ether. The reunited organic phases are dried, concentrated to dryness, and the residue is chromatographed on silica, eluting with a hexane-ethyl acetate mixture (8-2). 0.89 g of expected product is obtained, and 1.04 g of expected impure product is obtained, which is chromatographed again in the same conditions, and 0.75 g of expected product is recovered.

Workup

  1. waitfollowed by agitation for one and a half hours at -65° C
  2. customthe suspension obtained
  3. waitis left for half an hour at -65° C
  4. additionThe latter is added in small amounts and under inert atmosphere to a solution
  5. filtrationThe insoluble part is filtered off
  6. customdecanted
  7. washthe organic phase is washed with water
  8. extractionthe aqueous phases are extracted with isopropyl ether
  9. customThe reunited organic phases are dried
  10. concentrationconcentrated to dryness
  11. customthe residue is chromatographed on silica
  12. washeluting with a hexane-ethyl acetate mixture (8-2)

Sources & evidence

ORD record
ord-e313e4a19c064f738536ac610b0eb782
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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