1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22106969, compound

HRID 1456597Notes

Reaction equation

HRID 1456597 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[Cl-].[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:39]COC)=[C:17]([CH:38]=1)[CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][CH2:18][C:17]2[CH:38]=[C:13]([F:12])[CH:14]=[CH:15][C:16]=2[OH:39])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5880883,4-DifluorobenzaldehydeHCID 22441842HCID 22441842, compound

Product 1

HCID 22106969HCID 22106969, compound

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

610 mg of 3,4-difluorobenzaldehyde, 2000 mg of 5-fluoro-2-methoxymethoxybenzyltriphenylphosphonium chloride and 0.64 ml of DBU were allowed to react together in 20 ml of acetonitrile, subsequently treated, and purified by silica gel column chromatography, using a 15:1 by volume mixture of hexane and ethyl acetate as the eluent, in the same manner as described in Preparation 2, to give 1230 mg of an oily substance. This oily substance was dissolved in 10 ml of ethanol, and 300 mg of tris-(triphenylphosphine)rhodium(I) chloride were added to the resulting solution. The resulting mixture was then stirred under a hydrogen atmosphere at atmospheric pressure and at 60° C. for 14 hours. At the end of this time, the reaction solution was filtered with a Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure, and allowed to adsorb on a silica gel column for some time. The filtrate was then allowed to elute slowly, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give an eluate containing the title compound. This eluate was concentrated by evaporation under reduced pressure, and dried in vacuo, to give 1010 mg (yield 93%) of the title compound as a solid substance.

Workup

  1. additionsubsequently treated
  2. custompurified by silica gel column chromatography
  3. additionby volume mixture of hexane and ethyl acetate as the eluent
  4. customin the same manner as described in Preparation 2
  5. customto give 1230 mg of an oily substance
  6. filtrationAt the end of this time, the reaction solution was filtered with a Celite (trade mark)
  7. filtrationfilter aid
  8. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  9. washto elute slowly
  10. additionby volume mixture of hexane and ethyl acetate as the eluent
  11. customto give an eluate

Sources & evidence

ORD record
ord-83a122d35097444db68ab8097d408cf4
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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