Propylethinylcarbinol → HCID 178450439, compound

HRID 1764995Notes

Reaction equation

HRID 1764995 reaction equation
I[C:2]1[C:3]([F:25])=[C:4]([F:24])[C:5]([F:23])=[C:6]([C@H:8]2[CH2:13][CH2:12][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:7]=1.[CH:26]#[C:27][CH:28]([OH:32])[CH2:29][CH2:30][CH3:31].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Cu](I)I.CN(C=O)C.C(N(CC)CC)C>[OH:32][CH:28]([CH2:29][CH2:30][CH3:31])[C:27]#[C:26][C:2]1[C:3]([F:25])=[C:4]([F:24])[C:5]([F:23])=[C:6]([C@H:8]2[CH2:9][CH2:10][C@H:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)[CH:7]=1

Participants

7

Reactant 3

HCID 7746PropylethinylcarbinolHCID 24477Sodium ThiosulfateHCID 178448027HCID 178448027, compound

Product 1

HCID 178450439HCID 178450439, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

In a nitrogen atmosphere, 25 g of 5-iodo-2,3,4-trifluoro-1-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene was dissolved into 300 mL of DMF, to which 21 mL of triethylamine, 0.19 g of copper iodide (I), and 0.58 g of tetrakistriphenylphosphine palladium (0) were added, followed by heating to 55° C. Into this, the DMF (30 mL) solution containing 5.9 g of 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 sequentially carrying out column chromatography (silica gel, toluene) twice, activated carbon treatment (acetone), and column chromatography (silica gel, hexane/acetone), to obtain 20 g of 5-(3-hydroxy-1-hexynyl)-2,3,4-trifluoro-1-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene.

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

Sources & evidence

ORD record
ord-5ea5b98d566b4cfb87c9cb22b57d8ba9
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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