Carbon Tetrachloride → HCID 15201282, compound

HRID 461698Notes

Reaction equation

HRID 461698 reaction equation
[C:1]([O:17][CH3:18])(=[O:16])/[CH:2]=[C:3](\[CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10]CC=C(C)C)\[CH3:9])/C.[C:19](Cl)(Cl)(Cl)Cl>>[CH3:19]/[C:2](=[CH:3]\[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])/[C:1]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 5943Carbon TetrachlorideHCID 12527597HCID 12527597, compound

Product 1

HCID 15201282HCID 15201282, compound

Procedure

Gamma-Alkylation of Senecioic Acid (5) with Geranyl Bromide, Farnesoic Acids, (Method B) -- The copper dienolate from 1 g (0.01 mol) of senecioic acid (5) was formed by initial mixed dienolate generation (Method II) and subsequent addition of 3.89 g (0.02 mol) of cuprous iodide, and 5.0 g (0.025 mol) of geranyl bromide was added as in alkylation B. Isolation by procedure 3 and methylation with diazomethane produced 2.06 g (80%) of a mixture of esters. Using glpc analysis (Col. B, 145°), three major product peaks were found in a ratio of 10:36:54, A (retention time of 4 min.): B (retention time of 6.2 min.): C (retention time of 7.3 min.). Peak A was presumed to be the alpha product, and peaks B and C were identified as the isomeric gamma products by pmr (J. W. K. Burrell et al., J. Chem. Soc., 2144(1966)), after isolation by preparative glpc (Col. D). Methyl (Z,E)-farnesoate (Peak B): pmr (CCl4) δ 5.55 (s,1), 5.1-4.9 (m,2), 3.54 (s,3), 2.58 (t,2), 2.2-1.9 (m,6), 1.82 (d, J=0.5 Hz,3), 1.6 (s,3), and 1.4 (s,6).

Workup

  1. customanalysis (Col. B, 145°), three major product peaks

Sources & evidence

ORD record
ord-bdfb005f4fd44772ae2db497e2a60191
Source dataset
uspto-grants-1977_12
Patent number
US04064150

Reaction notes

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