Ethanol → Adamantane

HRID 1451693Notes

Reaction equation

HRID 1451693 reaction equation
C(O)C.COC1C=CC([C:10](Cl)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:11]2[CH:16]=CC(OC)=C[CH:12]=2)=CC=1>C1COCC1.Cl.N1C=CC=CC=1>[CH:11]12[CH2:10][CH:19]3[CH2:20][CH:21]([CH2:22][CH:23]([CH2:24]3)[CH2:16]1)[CH2:12]2

Participants

6

Reactant 2

HCID 702Ethanol2×HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Product 1

HCID 9238Adamantane

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To prepare compound 5 (1-O-(4,4'-dimethoxytrityl)-3-O-(N-adamantoyl-3-aminopropyl) glycerol), 8.56 g, (24.35 mmole) compound 4 was dissolved in a mixture of THF (48.7 ml) and 1M aqueous HCl (48.7 ml). The solution was stirred at room temperature for 30 minutes. 50 ml absolute ethanol (50 ml) was then added. The solution was concentrated, the residue was redissolved in 50 ml absolute ethanol, and the solution concentrated again. The resultant product was dried by co-evaporation with pyridine (2×50 ml) to give an oil which was redissolved in dry pyridine (150 ml). 8.25 g (24.35 mmole) 4,4'-dimethoxytrityl chloride was then added in two portions with stirring for 15 minutes. The resulting solution was left for 1 hour. 50 ml absolute ethanol was added and the solution was concentrated. The residue was dissolved in 200 ml dichloromethane and then washed with saturated sodium bicarbonate solution (2×60 ml). The aqueous layer was washed with dichloromethane (2×30 ml) and the organic extracts were combined, dried and evaporated. The residue was chromatographed on silica column (300 g) and eluted with a mixture of dichloromethane: methanol (19:1) to give a white foamy product (9.16 g (61.3%).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was redissolved in 50 ml absolute ethanol
  3. concentrationthe solution concentrated again
  4. dry with materialThe resultant product was dried by co-evaporation with pyridine (2×50 ml)
  5. customto give an oil which
  6. stirringwith stirring for 15 minutes
  7. waitThe resulting solution was left for 1 hour
  8. concentrationthe solution was concentrated
  9. dissolutionThe residue was dissolved in 200 ml dichloromethane
  10. washwashed with saturated sodium bicarbonate solution (2×60 ml)
  11. washThe aqueous layer was washed with dichloromethane (2×30 ml)
  12. customdried
  13. customevaporated
  14. customThe residue was chromatographed on silica column (300 g)
  15. washeluted with a mixture of dichloromethane: methanol (19:1)
  16. customto give a white foamy product (9.16 g (61.3%)

Sources & evidence

ORD record
ord-ee79dc4d8e1d48688a778950c8f165f7
Source dataset
uspto-grants-1997_02
Patent number
US05605890

Reaction notes

Loading…