Tetrahydrofuran → HCID 86669119, compound

HRID 1041829Notes

Reaction equation

HRID 1041829 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][C:25]=1[CH:31]1[CH2:34][CH2:33][CH2:32]1.C1(P(C2CCCCC2)C2C=[CH:46][CH:45]=[CH:44][C:43]=2[C:48]2[C:53](OC)=[CH:52][CH:51]=[CH:50][C:49]=2OC)CCCCC1.[CH2:64]1COC[CH2:65]1>CCCCCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:24]2[CH:29]=[CH:28][C:27]([C:64]#[C:65][C:51]3[CH:50]=[CH:49][C:48]([CH2:43][CH2:44][CH2:45][CH3:46])=[CH:53][CH:52]=3)=[CH:26][C:25]=2[CH:31]2[CH2:34][CH2:33][CH2:32]2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 27751321-Butyl-4-ethynylbenzeneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 68152517HCID 68152517, compound

Product 1

HCID 86669119HCID 86669119, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8058HexaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

7.8 g (47.0 mmol) of 1-butyl-4-ethynylbenzene are initially introduced in 100 ml of THF under nitrogen, cooled to −78° C., and 63.32 ml (63.20 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in hexane are added dropwise. After 1 hour, 63.22 ml (63.20 mmol) of a 1M solution of 9-methoxy-9-BBN in hexane are added, and the mixture is left to stir at −78° C. for 2 hours. In a second apparatus, 6.8 g (23.45 mmol) of 5, 0.916 g (1.0 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.64 g (4.0 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl are initially introduced in 100 ml of THF. The first solution is slowly added dropwise, and the batch is heated at 100° C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography and recrystallised from isopropanol, giving the title compound 3 as a solid.

Workup

  1. waitthe mixture is left
  2. additionThe first solution is slowly added dropwise
  3. temperaturethe batch is heated at 100° C. overnight
  4. extractionthe mixture is extracted twice with methyl t-butyl ether (100 ml)
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue is purified by column chromatography
  9. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-a63155b5dbe54267bc6c962133b02592
Source dataset
uspto-grants-2013_10
Patent number
US08557142B2

Reaction notes

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