2-Iodotoluene → HCID 23049346, compound

HRID 2106873Notes

Reaction equation

HRID 2106873 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-1be38ec2aff94d26ba209bbc55fd352e
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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