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 1108173

Reaction equation

HRID 1108173 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-92d507764bac4f08816881f205c8fc7c
Source dataset
uspto-grants-2000_05
Patent number
US06063360

Linked notes

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