Dimethylformamide → HCID 19102568, compound

HRID 1198546Notes

Reaction equation

HRID 1198546 reaction equation
[H-].[Na+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])[CH3:5].[CH2:14]([O:21][C:22]1[C:30]2[NH:29][CH:28]=[CH:27][C:26]=2[C:25](C=O)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:33]N(C)C=O>O1CCCC1>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25](/[CH:5]=[CH:4]/[C:6]([O:8][CH3:33])=[O:7])=[C:26]2[C:30]=1[NH:29][CH:28]=[CH:27]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 132434867-(Benzyloxy)-1H-indole-4-carbaldehydeHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 19102568HCID 19102568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60% Sodium hydride dispersion (0.10 g, 2.5 mmol) was added to a stirred solution of trimethylphosphonoacetate (0.41 ml, 2.5 mmol) in tetrahydrofuran (10 ml). The pale suspension was stirred for 1 hour at room temperature then a solution of 7-benzyloxyindole-4-carboxaldehyde (0.63 g, 2.5 mmol) in tetrahydrofuran (5 ml) was added followed by dimethylformamide (5 ml) to give a clear solution. The solution was stirred for 1 hour at room temperature then evaporated under high vacuum. The residue in ethyl acetate was washed with dilute hydrochloric acid dried and concentrated to give pale solid.

Workup

  1. customto give a clear solution
  2. stirringThe solution was stirred for 1 hour at room temperature
  3. customthen evaporated under high vacuum
  4. washThe residue in ethyl acetate was washed with dilute hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customto give pale solid

Sources & evidence

ORD record
ord-a22637df0ac647a783a8837d65e55557
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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