Barium manganate → HCID 13191778, compound

HRID 1285010Notes

Reaction equation

HRID 1285010 reaction equation
[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH2:19][OH:20])\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Mn]([O-])([O-])(=O)=O.[Ba+2]>ClCCl>[N:1]1([CH2:6]/[CH:7]=[C:8](/[C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH:19]=[O:20])\[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3084030Barium manganateHCID 13191776HCID 13191776, compound

Product 1

HCID 13191778HCID 13191778, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the above 3-(3-pyrrolidino-1-(4-tolyl)-prop-1E-enyl)benzyl alcohol (1.1 g) in dichloromethane (75 mL) was added barium manganate (Firouzabadi and Ghaderi, Tetrahedron Letters, 1978, 839) and the mixture was kept at 40° for 7 hours, and left at room temperature for 16 hours. The solid was removed by filtration and the filtrate was evaporated to give the crude 3-(3-pyrrolidino-1-(4-tolyl)prop-1E-enyl)benzaldehyde (1.09 g) which was not further purified. To a stirred suspension of sodium hydride (107 mg; 80% oil suspension) in 1,2-dimethoxyethane (3.7 mL) was added diethyl methoxycarbonylmethyl-phosphonate (740 mg) in 1,2-dimethoxyethane (3.7 mL). After 15 minutes' stirring, a solution of the above (E)-aldehyde (1.09 g) in 1,2-dimethoxyethane (3.7 mL) was added dropwise and the mixture was stirred for 18 hours at room temperature. After addition of water and acidification with dilute hydrochloric acid, the suspension was washed with ether, and the clear aqueous solution was basified with sodium carbonate solution and the precipitated oil was extracted into ether. The washed and dried ether solution was evaporated to leave a solid (800 mg) which was dissolved in ethanol and refluxed with Girard reagent P (200 mg) for 1 hour. The solvent was evaporated, water and ether were added and the ether extract was washed, dried and evaporated to leave methyl (E)-3-(3-pyrrolidino-1-(4-tolyl)prop-1E-enyl)cinnamate, m.p. 102°-107° (620 mg).

Workup

  1. waitleft at room temperature for 16 hours
  2. customThe solid was removed by filtration
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-6db53264a4f44e38af5a6e5484c504c7
Source dataset
uspto-grants-1986_01
Patent number
US04564685

Reaction notes

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