Boron trifluoride etherate → 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

HRID 2599

Reaction equation

HRID 2599 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:16]2[O:15][C:14]([CH3:18])([CH3:17])[O:13][C:12]=2[C:11]([C:19]([C:41]2[C:51]3[O:52][C:53]([CH3:56])([CH3:55])[O:54][C:50]=3[C:49]([C:57]([O:59][CH3:60])=[O:58])=[C:43]3[O:44][C:45]([CH3:48])([CH3:47])[O:46][C:42]=23)([C:21]2[C:31]3[S:32][C:33]([CH3:36])([CH3:35])[S:34][C:30]=3[C:29]([C:37]([O:39][CH3:40])=[O:38])=[C:23]3[S:24][C:25]([CH3:28])([CH3:27])[S:26][C:22]=23)O)=[C:10]2[C:6]=1[O:7][C:8]([CH3:62])([CH3:61])[O:9]2)=[O:4].B(F)(F)F.CCOCC.[Sn](Cl)Cl>[Zn]>[CH3:60][O:59][C:57]([C:49]1[C:50]2[O:54][C:53]([CH3:55])([CH3:56])[O:52][C:51]=2[C:41]([CH:19]([C:11]2[C:12]3[O:13][C:14]([CH3:18])([CH3:17])[O:15][C:16]=3[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]3[O:7][C:8]([CH3:61])([CH3:62])[O:9][C:10]=23)[C:21]2[C:31]3[S:32][C:33]([CH3:36])([CH3:35])[S:34][C:30]=3[C:29]([C:37]([O:39][CH3:40])=[O:38])=[C:23]3[S:24][C:25]([CH3:27])([CH3:28])[S:26][C:22]=23)=[C:42]2[C:43]=1[O:44][C:45]([CH3:48])([CH3:47])[O:46]2)=[O:58]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24479Stannous ChlorideHCID 86752299Bis-(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

Product 1

HCID 86752298Bis-(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

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

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.

Workup

  1. customin dry
  2. customdegassed acetonitrile under an argon atmosphere
  3. customThe product was purified by flash chromatography (ether/heptane 5:1)

Sources & evidence

ORD record
ord-71815a1699b6445f9f96283c7d73efe0
Source dataset
uspto-grants-1998_03
Patent number
US05728370

Linked notes

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