1-Iodonaphthalene → 5-(1-Naphthyl)-4-pentyn-1-ol

HRID 1990702Notes

Reaction equation

HRID 1990702 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].I[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(#N)C>[C:16]1([C:5]#[C:4][CH2:3][CH2:2][CH2:1][OH:6])[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 70041-IodonaphthaleneHCID 8471TriethylamineHCID 793464-Pentyn-1-ol

Product 1

HCID 199555575-(1-Naphthyl)-4-pentyn-1-olYield 82.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 0.59 g (7 mmol) of 4-pentyn-1-ol in 3 ml of acetonitrile is added dropwise under an argon atmosphere to a suspension of 1.78 g (7 mmol) of 1-iodonaphthalene, of 1.48 ml (10.5 mmol) of triethylamine, of 0.066 g (0.35 mmol) of cuprous iodide and of 0.147 g (0.21 mmol) of di(triphenylphosphine)palladium dichloride (Ph3P)2PdCl2 in 4 ml of acetonitrile. The mixture is stirred at ambient temperature for 3 hours, 4 g of silica are then added and the mixture is evaporated to dryness. The product is purified by chromatography on silica gel, elution being carried out with an 80/20 and then 60/40 mixture of cyclohexane and of ethyl acetate, to produce 1.22 g of product in the form of a yellow oil.

Workup

  1. addition4 g of silica are then added
  2. customthe mixture is evaporated to dryness
  3. customThe product is purified by chromatography on silica gel, elution
  4. addition60/40 mixture of cyclohexane

Sources & evidence

ORD record
ord-0e24158261e141b191a3dcee34a14136
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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