3,4-Diisopropoxy-3-cyclobutene-1,2-dione → 3-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione

HRID 1591273Notes

Reaction equation

HRID 1591273 reaction equation
CC(O[C:5]1[C:9](=[O:10])[C:7](=[O:8])[C:6]=1[O:11][CH:12]([CH3:14])[CH3:13])C.[Sn:15]([Si](C)(C)C)([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH3:14][CH:12]([O:11][C:6]1[C:7](=[O:8])[C:9](=[O:10])[C:5]=1[Sn:15]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13]

Participants

5

Reactant 2

HCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 178448237HCID 178448237, compound

Product 1

HCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dioneYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.052M n-Bu4N+CN- in tetrahydrofuran (7.69 mL, 0.4 mmol) was added dropwise to a stirred solution at -20° C. of diisopropyl squarate (3.96 g, 0.020 mol) and n-Bu3SnSi(CH3)3 (7.27 g, 0.020 mol) in tetrahydrofuran (154 mL). Stirring was continued at -20° C. for 2 hrs. The solution was concentrated and the residue chromatographed on SiO2 with diethyl ether-hexane (10:90) to afford the title compound (5.75 g, 67% yield) as a yellow oil.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue chromatographed on SiO2 with diethyl ether-hexane (10:90)

Sources & evidence

ORD record
ord-5601b47117d644ff87fcd5212c7d2e0d
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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