Carbon Tetrachloride → HCID 19375761, compound

HRID 2211378Notes

Reaction equation

HRID 2211378 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][C:5]=1[O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:20])([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:13]#[N:14])(=O)[CH3:2].C(Cl)(Cl)(Cl)Cl.FC(F)(F)C(O)=O>C([SiH](CC)CC)C>[CH3:20][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:21]=[C:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:23]=[CH:24][C:4]=1[CH2:1][CH3:2])[C:13]#[N:14]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 6422Trifluoroacetic acidHCID 19375766HCID 19375766, compound

Product 1

HCID 19375761HCID 19375761, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

7-(2-Acetyl-5-benzyloxyphenoxy)-2-methyl-2-n-pentylheptanenitrile was dissolved in carbon tetrachloride containing 6 equivalents of triethylsilane. After addition of 60 equivalents of trifluoroacetic acid, the solution was stirred 24 hours and then evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether to provided the title product as an oil in 90% yield, NMR.

Workup

  1. customevaporated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether

Sources & evidence

ORD record
ord-8a6df4734e684d84bbca555c37eb5c4f
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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