1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22106926, compound

HRID 1456593Notes

Reaction equation

HRID 1456593 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].[Cl-].[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:40]COC)=[C:18]([CH:39]=1)[CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1CCN2C(=NCCC2)CC1.S([O-])(O)=O.[Na+]>C(#N)C.C1C=CC=CC=1.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:13][C:14]1[CH:15]=[CH:16][C:17]([OH:40])=[C:18]([CH2:19][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[C:3]([O:10][CH3:11])[CH:4]=2)[CH:39]=1

Participants

9

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 22441842HCID 22441842, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 22106926HCID 22106926, compoundYield 83.7%

Reagents, catalysts & solvents 4

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

547 mg of 4-fluoro-3-methoxybenzaldehyde, 1990 mg of 5-fluoro-2-methoxymethoxybenzyltriphenylphosphonium chloride (prepared as described in Preparation 8) and 0.58 ml of DBU were allowed to react together in 30 ml of acetonitrile, subsequently treated, and purified by silica gel column chromatography, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, in the same manner as described in Preparation 2, to give 948 mg of an oily substance. 936 mg of this oily substance were dissolved in 9 ml of a 1:2 by volume mixture of benzene and ethanol, and then 155 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. A saturated aqueous solution of sodium hydrogen sulfite was then added to the reaction mixture and the mixture was then stirred for about 10 minutes. The resulting insoluble substances were then removed by filtration using a Celite (trade mark) filter aid. The filtrate was concentrated by evaporation under reduced pressure, and purified by silica gel column chromatography, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 785 mg (yield 73%) of the title compound as an oily 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 948 mg of an oily substance
  6. stirringthe mixture was then stirred for about 10 minutes
  7. customThe resulting insoluble substances were then removed by filtration
  8. filtrationfilter aid
  9. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  10. custompurified by silica gel column chromatography
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-01364ed2e0bc40debd12d9d80aa12ad4
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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