Ethanol → HCID 573574, compound

HRID 2163627Notes

Reaction equation

HRID 2163627 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[CH:13](Cl)(Cl)Cl.[CH3:17][CH2:18]O>CCOCC.[Zn+2].[Br-].[Br-]>[CH3:12][C:2]1[C:7](=[O:1])[CH2:6][CH2:5][CH:4]([CH:18]([CH3:17])[CH3:13])[CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 6212ChloroformHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 573574HCID 573574, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of MICO (4.4 mg, 2.9 × 10-2 mmol), a trace of p-toluenesulfonic acid monohydrate and CHCl3 (3 mL) was refluxed for 30 min, taken up in 30 mL of ether and worked up as previously described for the ZnBr2 rearrangement to yield an oily residue. One major product (>95% of total volatiles) was isolated by VPC and shown to be the desired -2-en- analog by comparison of IR and MS spectra with those of authentic materials. UV (95% EtOH) lambda(max) = 227 nm; IR 2950, 1680 (C=0), 1355 and 1375(d), 1125, 1103, 1072(d). MS m/e (rel abundance) 153(9), 152(57), 137(9), 111(10), 110(100), 109(58), 97(23), 96(19), 95(73), 81(43).

Workup

  1. additionA mixture of MICO (4.4 mg, 2.9 × 10-2 mmol)
  2. customto yield an oily residue
  3. customOne major product (>95% of total volatiles) was isolated by VPC

Sources & evidence

ORD record
ord-d0191acde37942f9b13de7041322f166
Source dataset
uspto-grants-1979_01
Patent number
US04136119

Reaction notes

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