Reaction #2695

ord-71815a1699b6445f9f96283c7d73efe0

Reaction equation

COC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2
Bis-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol
CCOCC.FB(F)F
BF3.Et2O
[Cl][Sn][Cl]
tin(II) chloride
→
COC(=O)c1c2c(c(C(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2
Bis-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis (1,3) dioxol-4-yl)-mono-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl) methane

Reactants

COC(=O)c1c2c(c(C(O)(c3c4c(c(C(=O)OC)c5c3OC(C)(C)O5)OC(C)(C)O4)c3c4c(c(C(=O)OC)c5c3SC(C)(C)S5)SC(C)(C)S4)c3c1OC(C)(C)O3)OC(C)(C)O2
Bis-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol
CCOCC.FB(F)F
BF3.Et2O
[Cl][Sn][Cl]
tin(II) chloride

Reagents

[Zn]
zinc

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherin dry
  2. 2
    Otherdegassed acetonitrile under an argon atmosphere
  3. 3
    OtherThe product was purified by flash chromatography (ether/heptane 5:1)

Procedure

Bis-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxol-4-yl)-mono-(8-methoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dithiol-4-yl)methanol (5 mg, 0.005 mmol) was dissolved in dry, degassed acetonitrile under an argon atmosphere. BF3.Et2O (2.0 μL, 0.011 mmol) and tin(II) chloride (3.0 mg, 0.016 mmol) were added. Amalgamated zinc (1.0 mg, 0.015 mmol) was added. The product was purified by flash chromatography (ether/heptane 5:1). Due to the small amount used the yield was not determined.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728370uspto-grants-1998_03