1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 17952717, compound

HRID 1394635Notes

Reaction equation

HRID 1394635 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[C:2]1[CH:8]=O.COP([CH:16]([NH:20]C(=O)C)[C:17](=[O:19])[CH3:18])(=O)OC.C1CCN2C(=NCCC2)CC1>ClCCl>[S:1]1[C:2]2=[CH:8][N:20]=[C:16]([C:17](=[O:19])[CH3:18])[CH:6]=[C:3]2[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 573752Thiophene-2,3-dicarbaldehydeHCID 10900225HCID 10900225, compound

Product 1

HCID 17952717HCID 17952717, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,3-thiophenedicarboxaldehyde (600 mg, 4.28 mmol) in dichloromethane (50 ml) was cooled to 0° C. under an atmosphere of nitrogen. (1-Acetylamino-2-oxo-propyl)-phosphonic acid dimethyl ester (1.05 g, 4.70 mmol) was added [literature procedure: Kitamura, et al. Tet. Lett., 36(32), 1995, pp. 5769-5772], followed by DBU (0.471 ml, 4.70 mmol), and the mixture allowed to warm to ambient temperature overnight, then concentrated in vacuo, and the residue was then purified by flash chromatography (0-50% ethyl acetate in hexanes) to provide 1-thieno[2,3-c]pyridin-5-yl-ethanone as a white solid (326 mg, 43%). 1HNMR (250 MHz, CDCl3): δ 9.20 (s, 1H), 8.50 (d, 1H, J=1.02), 7.80 (d, 1H, J=5.36), 7.51 (d, 1H, J=5.36), 2.81 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was then purified by flash chromatography (0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ecfad03223024fe8b8e611a8e1550ebe
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

Loading…