2-Iodotoluene → HCID 23049346, compound

HRID 1722235Notes

Reaction equation

HRID 1722235 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14]>C(NCC)C>[CH3:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]#[C:4][CH2:3][CH2:2][CH2:1][OH:6]

Participants

4

Reactant 2

HCID 51282-IodotolueneHCID 793464-Pentyn-1-ol

Product 1

HCID 23049346HCID 23049346, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

A mixture of 4-pentyn-1-ol (1 g, 12.1 mmol), 2-iodotoluene (2.53 g, 11.6 mmol), dry diethylamine (20 ml), bis-triphenyl-phosphine palladium (II) chloride (150 mg) and cuprous iodide (60 mg) was stirred at room temperature under dry nitrogen for 24 hours). The solvent was removed and the residue extracted with ether. The organic phase was washed with brine and dried and the solvent removed. The crude product was purified by dry column chromatography (alumina, 9:1 hexane:ether 1:1 hexane:ether) to give 1.2 g (60% of theory) of 5-(2'-methylphenyl)-4-pentyn-1-ol as a brown oil.

Workup

  1. customThe solvent was removed
  2. extractionthe residue extracted with ether
  3. washThe organic phase was washed with brine
  4. customdried
  5. customthe solvent removed
  6. customThe crude product was purified
  7. dry with materialby dry column chromatography (alumina, 9:1 hexane:ether 1:1 hexane:ether)

Sources & evidence

ORD record
ord-0419a53ef3be40ed80c13c6799b81a9f
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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