5-Hexyn-1-ol → HCID 15117022, compound

HRID 982341Notes

Reaction equation

HRID 982341 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:10]([OH:16])[CH2:11][CH2:12][CH2:13][C:14]#[CH:15]>C(N(CC)CC)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:16][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[C:15][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 702345-Hexyn-1-olHCID 811292-Bromobenzaldehyde

Product 1

HCID 15117022HCID 15117022, compound

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-bromobenzaldehyde (5.0 g, 27.0 mmol) and 5-hexyn-1-ol (3.18 g, 32.0 mmol) in triethyl amine (100 mL) was added bis(triphenylphosphine)palladium (II) dichloride (0.28 g, 0.4 mmol) and cuprous iodide (51 mg, 0.27 mmol). After heating the resulting mixture to reflux under an argon atmosphere for 1 hour, the reaction mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel chromatography eluting with 2:1 diethyl ether/hexanes to afford a yellow oil.

Workup

  1. temperatureAfter heating the resulting mixture
  2. temperatureto reflux under an argon atmosphere for 1 hour
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography
  6. washeluting with 2:1 diethyl ether/hexanes
  7. customto afford a yellow oil

Sources & evidence

ORD record
ord-963a92e8693344de89f87f146b4e9461
Source dataset
uspto-grants-1991_02
Patent number
US04996214

Reaction notes

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