Water → HCID 15044216, compound

HRID 1067055Notes

Reaction equation

HRID 1067055 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C)(C)[O:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([O:21][Si](C)(C)C)[C:19]#N)=[CH:14][CH:13]=1.[OH2:28]>C(OCC)C>[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[OH:28])=[O:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13584732HCID 13584732, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 15044216HCID 15044216, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Following the method of Krepski et al., Tetrahedron Lett., 1983, 24, 4075-78, 185 mL of a 3.0 M phenylmagnesium bromide solution in diethyl ether (Aldrich) was added to a stirred solution of 143 g (0.49 mol) 4-trimethylsilyloxy-α-trimethylsilyloxyphenylacetonitrile from Example 54 in 1.0 L diethyl ether at 0° C. When addition was complete, the solution was allowed to stand at room temperature overnight before 50 mL water was added slowly.

Workup

  1. additionWhen addition
  2. additionwas added slowly

Sources & evidence

ORD record
ord-7f201f72a4ec41c4aa046613905793de
Source dataset
uspto-grants-2001_06
Patent number
US06245922B1

Reaction notes

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