1,4-Bis(diphenylphosphino)butane → HCID 89610333, compound

HRID 1518939Notes

Reaction equation

HRID 1518939 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9](OS(C(F)(F)F)(=O)=O)=[C:8]([O:20][CH3:21])[CH:7]=1.[CH2:22]([N:25]1[C:29](=[O:30])[CH2:28][CH2:27][C:26]1=[O:31])[C:23]#[CH:24].C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.[Cu]I>[O:31]=[C:26]1[CH2:27][CH2:28][C:29](=[O:30])[N:25]1[CH2:22][C:23]#[C:24][C:9]1[CH:10]=[CH:11][C:6]([CH:2]=[O:3])=[CH:7][C:8]=1[O:20][CH3:21]

Participants

6

Reactant 3

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 4737238SBB039933HCID 89610444HCID 89610444, compound

Product 1

HCID 89610333HCID 89610333, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.26 g (15 mmol) triflate (6.1b), 2.47 g (18 mmol) of 1-prop-2-ynyl-pyrrolidine-2,5-dione (7.4), 0.067 g (0.3 mmol) of [(C6H5)3P]2PdCl2, 0.143 g (0.75 mmol) CuI, 0.32 g (0.75 mmol) of 1,4-bis(diphenyl-phosphino)butane and 7 ml (50.5 mmol) of TEA in 40 ml DMF under nitrogen at 100° C. for 3 h. The inorganic salts are removed and DMF is evaporated. The residue is treated with water, extracted 3×50 ml of EtOAc, the collected organic phase is evaporated and purified by flash chromatography (toluene-MeOH 9:1). The desired intermediate 4.19 is 1.9 g (44%) of 4-[3-(2,5-dioxo-pyrrolidin-1-yl)-prop-1-ynyl]-3-methoxy-benzaldehyde, as a dark yellow solid. (M+H)+=272, Rt=2.15 min (A), purity: 98.9%.

Workup

  1. customThe inorganic salts are removed
  2. customDMF is evaporated
  3. additionThe residue is treated with water
  4. extractionextracted 3×50 ml of EtOAc
  5. customthe collected organic phase is evaporated
  6. custompurified by flash chromatography (toluene-MeOH 9:1)

Sources & evidence

ORD record
ord-f7ab601b2f20494faa7d9afc3ffba4d2
Source dataset
uspto-grants-2015_07
Patent number
US09073853B2

Reaction notes

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