HCID 67316907, compound → HCID 67316052, compound

HRID 1819622Notes

Reaction equation

HRID 1819622 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[N:18][S:19]([CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:21])=[O:20])=[C:9]1[CH3:30])([CH3:4])([CH3:3])[CH3:2].[CH:32]([Mg]Br)=[CH2:33]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]([NH:18][S:19]([CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:21])=[O:20])[CH:32]=[CH2:33])=[C:9]1[CH3:30])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 67316907HCID 67316907, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 67316052HCID 67316052, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

The product of step b) (2.2 g, 5 mmol) was treated with 100 mL toluene. The slurry was stirred at 0° C. and treated with Me3AI (3.8 mL of 2 M in toluene) followed by vinyl magnesium bromide (10 mL of 1 M). The reaction was warmed to rt and stirred for 10 minutes. The reaction was cooled to 0° C., quenched with aqueous acetic acid, and partitioned between water and EtOAc (200 mL each). The organic layer was washed with 1 M NaOH, dried over MgSO4 and purified over silica gel (30% EtOAc/Hex) to give 1.25 g of the sub-title compound as an oil.

Workup

  1. temperatureThe reaction was warmed to rt
  2. stirringstirred for 10 minutes
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched with aqueous acetic acid
  5. custompartitioned between water and EtOAc (200 mL each)
  6. washThe organic layer was washed with 1 M NaOH
  7. dry with materialdried over MgSO4
  8. custompurified over silica gel (30% EtOAc/Hex)

Sources & evidence

ORD record
ord-b140e79da94d4e33b3fcd7f3b3947a47
Source dataset
uspto-grants-2009_10
Patent number
US07601749B2

Reaction notes

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