HCID 59832526, compound → HCID 12162324, compound

HRID 605030Notes

Reaction equation

HRID 605030 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[C:13]([CH3:35])[CH:14]2[Si:20]([CH:23]1[C:31]2[C:26](=[C:27](Br)[C:28]([CH3:32])=[CH:29][CH:30]=2)[CH:25]=[C:24]1[CH3:34])([CH3:22])[CH3:21]>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]1([C:10]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]3[C:11]=2[CH:12]=[C:13]([CH3:35])[CH:14]3[Si:20]([CH:23]2[C:31]3[C:26](=[C:27]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:28]([CH3:32])=[CH:29][CH:30]=3)[CH:25]=[C:24]2[CH3:34])([CH3:22])[CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 59832526HCID 59832526, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 12162324HCID 12162324, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

In an argon atmosphere, to a solution of 15 mL of THF with 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF, 13.0 ml of 1.0 M phenylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 mmol) of 2 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.36 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.

Workup

  1. stirringThe resulting mixture was stirred for 5 hours
  2. temperatureat reflux
  3. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes)

Sources & evidence

ORD record
ord-c27a4a703a0f47b3b61ea140d605d063
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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