HCID 534076, compound → HCID 70653185, compound

HRID 2275394Notes

Reaction equation

HRID 2275394 reaction equation
C[Sn]1(C)[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:4]2[S:10][CH:11]=[CH:12][C:3]1=2.Br[C:15](Br)=[CH:16][CH2:17][CH2:18][CH3:19]>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:16](=[C:15]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:4]2[S:10][CH:11]=[CH:12][C:3]1=2)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 534076HCID 534076, compoundHCID 86688839HCID 86688839, compound

Product 1

HCID 70653185HCID 70653185, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.6 mmol) of 52 and 364 mg (1.6 mmol) of dibromopentene were dissolved in 32 ml of freshly distilled THF, and 42 mg (80 μmol) of bis(tri-tert-butylphosphine)palladium(0) were added. The reaction mixture was refluxed while stirring for 8 hours. THF was removed by rotary evaporation and the residue was taken up in n-hexane. The crude product was purified by means of column chromatography (n-hexane as the eluent (Rf=0.4)) to obtain 115 mg of the target compound 53 (37% yield). GC-MS m/z 232 (18.10 min).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed
  3. customTHF was removed by rotary evaporation
  4. customThe crude product was purified by means of column chromatography (n-hexane as the eluent (Rf=0.4))

Sources & evidence

ORD record
ord-d289abcd4d284d4ba8ed7126bc7a6281
Source dataset
uspto-grants-2015_09
Patent number
US09127020B2

Reaction notes

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