3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → 3-Methoxy-4-tributylstannanylcyclobut-3-ene-1,2-dione

HRID 1171898Notes

Reaction equation

HRID 1171898 reaction equation
CO[C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1[O:7][CH3:8].C[Si](C)(C)[Sn:13]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17]>C1COCC1.[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:8][O:7][C:6]1[C:5](=[O:9])[C:4](=[O:10])[C:3]=1[Sn:13]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 178448237HCID 178448237, compound

Product 1

HCID 586460293-Methoxy-4-tributylstannanylcyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 2

HCID 165872Tetrabutylammonium CyanideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,4-dimethoxy-cyclobut-3-ene-1,2-dione (1.5 g, 10.6 mmol) and trimethyl(tributylstannyl)silane (3.7 mL, 10.6 mmol) in anhydrous THF (75 mL) at −30° C. was added drop-wise a solution of tetrabutylammonium cyanide (57 mg, 0.2 mmol) in THF (3 mL). The clear solution quickly turned yellow and was left to warm to rt overnight. The reaction was concentrated in vacuo revealing a black oil which was dissolved in ether and filtered through a plug of silica (100% ether). The crude material was further purified by silica gel chromatography (100% hexanes to 3% Et2O in hexanes) to yield 3-methoxy-4-tributylstannanylcyclobut-3-ene-1,2-dione as a light yellow oil. 1H NMR (DMSO-d6, 400 MHz): δ0.90 (t, J=7.2 Hz, 9H), 1.09-1.23 (m, 6H), 1.23-1.38 (m, 6H), 1.43-1.63 (m, 6H), 4.38 (s, 3H).

Workup

  1. waitThe clear solution quickly turned yellow and was left
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionwas dissolved in ether
  4. filtrationfiltered through a plug of silica (100% ether)
  5. customThe crude material was further purified by silica gel chromatography (100% hexanes to 3% Et2O in hexanes)

Sources & evidence

ORD record
ord-d4358c275ab54317b132ee5ad29c860f
Source dataset
uspto-grants-2010_11
Patent number
US07829717B2

Reaction notes

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