Dabco → HCID 15370491, compound

HRID 1452406Notes

Reaction equation

HRID 1452406 reaction equation
[CH2:1]([CH:4]1[C:9]2[C:10](=[O:19])[C:11]3[C:16]([C:17](=[O:18])[C:8]=2[CH2:7][CH:6]([C:20]([O:22][CH3:23])=[O:21])[O:5]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:2][CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N12CCN(CC1)CC2>>[CH2:1]([CH:4]1[C:9]2[C:10](=[O:19])[C:11]3[C:16]([C:17](=[O:18])[C:8]=2[CH:7]=[C:6]([C:20]([O:22][CH3:23])=[O:21])[O:5]1)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 9237DabcoHCID 11776TriphenylphosphineHCID 15370489HCID 15370489, compound

Product 1

HCID 15370491HCID 15370491, compoundYield 70%

Procedure

The 1-propyl-3-methoxycarbonyl-3,4,5,10-tetrahydro-5,10-dioxo-1H-naphtho-[2,3-c]-pyran described in step 4 (50 mg, 0.159 mmol) was stirred with triphenylphosphine (166.6 mg, 0.636 mmol) and 1,4-diaza bicyclo-[2,2.2]-octane (19.6 mg, 0.175 mmol) in presence of air for a few hours at room temperature until the starting material was entirely consumed. The reaction mixture was evaporated to dryness. The crude product obtained was chromatographed (toluene/ethyl acetate=10/1, v/v) to give the titled compound (35 mg, 70%).

Workup

  1. customwas entirely consumed
  2. customThe reaction mixture was evaporated to dryness
  3. customThe crude product obtained
  4. customwas chromatographed (toluene/ethyl acetate=10/1

Sources & evidence

ORD record
ord-b6b6654a36e2429cbb12cad4915a2d9d
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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