Propylethinylcarbinol → HCID 23115712, compound

HRID 1764999Notes

Reaction equation

HRID 1764999 reaction equation
[CH:1]#[C:2][CH:3]([OH:7])[CH2:4][CH2:5][CH3:6].S([O-])([O-])(=O)=S.[Na+].[Na+].I[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:17]=1[F:24]>CN(C=O)C.C(N(CC)CC)C.[Cu](I)I>[OH:7][CH:3]([CH2:4][CH2:5][CH3:6])[C:2]#[C:1][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[C:17]=1[F:24]

Participants

7

Reactant 3

HCID 7746PropylethinylcarbinolHCID 24477Sodium ThiosulfateHCID 27792531,2,3-Trifluoro-4-iodobenzene

Product 1

HCID 23115712HCID 23115712, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolventHCID 83717Copper iodideSolvent

Conditions

Temperature
55 °C

Procedure

In a nitrogen atmosphere, 4-iodo-1,2,3-trifluorobenzene was dissolved into DMF, into which triethylamine, copper iodide (I), and tetrakistriphenylphosphine palladium (0) were added and heated to 55° C. Then, the DMF solution containing 1-hexine-3-ol was added dropwise for 20 minutes, and stirred for 3 hours. After the reaction mixture was poured into a sodium thiosulfate aqueous solution, and stirred for a while, an organic layer was separated, and an aqueous layer was extracted with toluene. After the extract and the organic layer were mixed together, washed using water, 10% hydrochloric acid twice, water, a saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in that order, and dried using anhydrous magnesium sulfate, the solvent was evaporated under a reduced pressure. The residue was purified by column chromatography (silica gel, toluene/hexane) to obtain 1-(3-hydroxy-1-hexynyl)-2,3,4-trifluorobenzene.

Workup

  1. additionwere added
  2. additionwas added dropwise for 20 minutes
  3. stirringstirred for a while
  4. customan organic layer was separated
  5. extractionan aqueous layer was extracted with toluene
  6. extractionAfter the extract
  7. additionthe organic layer were mixed together
  8. washwashed
  9. dry with materialwater, a saturated sodium hydrogen carbonate aqueous solution, and a saturated saline solution in that order, and dried
  10. customthe solvent was evaporated under a reduced pressure
  11. customThe residue was purified by column chromatography (silica gel, toluene/hexane)

Sources & evidence

ORD record
ord-2ea8aa046b1043538a0c3827bc9bb26d
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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