Hexane → HCID 13231532, compound

HRID 2261509Notes

Reaction equation

HRID 2261509 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][Bi:11](Br)[CH3:12].CCCCCC>C(OCC)C.C1COCC1>[CH3:10][Bi:11]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:12]

Participants

6

Reactant 3

HCID 8058HexaneHCID 13117945HCID 13117945, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 13231532HCID 13231532, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 40 ml (40 mmole) of 1.0 M solution of benzyl magnesium chloride in diethyl ether was cooled to 0° C., and thereto was added dropwise a solution of 10.2 g (32.1 mmole) of dimethylbismuthanyl bromide prepared in Preparation Example 2 in 20 ml of THF (45 minutes). The reaction mixture was further stirred at 0° C. for 2 hours qnd hexane was added. The supernatant liquid was extracted, concentrated and distilled in a vacuum, giving 3.5 g (yield 32.8%) of a yellow liquid product. b.p. 67-76° C./0.7 mmHg. 1H-NMR revealed that the product was the desired one.

Workup

  1. additionwas added
  2. extractionThe supernatant liquid was extracted
  3. concentrationconcentrated
  4. distillationdistilled in a vacuum

Sources & evidence

ORD record
ord-78beb28510b54e35a2ca350238189cdc
Source dataset
uspto-grants-2010_12
Patent number
US07847043B2

Reaction notes

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