1-Pentyne → Ethyl (3-(pentyne-1-yl)phenyl)acetate

HRID 475545Notes

Reaction equation

HRID 475545 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:33]#[C:34][CH2:35][CH2:36][CH3:37]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:33]([C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)#[C:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 123091-PentyneHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

Product 1

HCID 67100180Ethyl (3-(pentyne-1-yl)phenyl)acetateYield 80.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl (3-bromophenyl)acetate (0.3 g, 1.24 mmol) and tetrabutylammonium fluoride hydrate (0.97 g, 3.72 mmol), was treated with PdCl2(PPh3)2 (26 mg, 0.037 mmol; 3 mole %) and 1-pentyne (367 μl, 3.72 mmol) in a sealed tube. The tube was heated at 80° C. for 2 h. The mixture was treated with water, and was extracted with diethyl ether. The organic extract was dried over sodium sulfate, filtered and evaporated in vacuo to give the crude product. Purification on a Biotage™ 25M column (silica), eluting with ethyl acetate/hexane 0:1 to 2:98, gave ethyl (3-(pentyne-1-yl)phenyl)acetate as a pale yellow oil (0.23 g, 79%).

Workup

  1. extractionwas extracted with diethyl ether
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customPurification on a Biotage™ 25M column (silica)
  8. washeluting with ethyl acetate/hexane 0:1 to 2:98

Sources & evidence

ORD record
ord-0de08e7b90404ea7ae14f2aa9466c317
Source dataset
uspto-grants-2014_01
Patent number
US08637574B2

Reaction notes

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