Triphenylphosphine → (+)-6-Decyloxy-2-(3-hydroxy-1-butynyl)naphthalene

HRID 1734395Notes

Reaction equation

HRID 1734395 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17](Br)[CH:16]=[CH:15]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:23][CH:24]([OH:27])[C:25]#[CH:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu](I)I.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.C(NCC)C>[CH2:1]([O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([C:26]#[C:25][CH:24]([OH:27])[CH3:23])[CH:16]=[CH:15]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 162393-Butyn-2-olHCID 6138212-Bromo-6-decyloxynaphthalene

Product 1

HCID 19437538(+)-6-Decyloxy-2-(3-hydroxy-1-butynyl)naphthaleneYield 81%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

18.2 g (0.05 mol) of 6-decyloxy-2-bromonaphthalene (VI-59), 10.5 g (0.15 mol) of (+)-3-butyn-2-ol (VII*-59), 0.4 g of copper iodide, 0.7 g of triphenylphosphine, 0.4 g of bis(triphenylphosphine)palladium chloride and 100 ml of diethylamine were stirred under reflux for 12 hours in an atmosphere of nitrogen gas. After completion of the reaction, the reaction mixture was poured into ice/aqueous hydrochloric acid and extracted with 200 ml of ethyl acetate. The organic layer was further washed with water and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene-ethyl acetate as eluent to obtain 14.3 g (yield 81%) of optically active (+)-6-decyloxy-2-(3-hydroxy-1-butynyl)naphthalene (I'-59), mp 74°-75° C. [α]D20 =+16.9° (c=1, chloroform).

Workup

  1. temperatureunder reflux for 12 hours in an atmosphere of nitrogen gas
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into ice/aqueous hydrochloric acid
  4. extractionextracted with 200 ml of ethyl acetate
  5. washThe organic layer was further washed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5a22831c6a0a403a84c01872963ac725
Source dataset
uspto-grants-1996_07
Patent number
US05534188

Reaction notes

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