Water → HCID 19008982, compound

HRID 1742218Notes

Reaction equation

HRID 1742218 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C.[CH:8]([N-]C(C)C)(C)C.[Li+].[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29]Br)=[CH:24][CH:23]=2)=[CH:19][CH:18]=1.O>O1CCCC1>[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:8][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[CH:24][CH:23]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79752-MethylpyridineHCID 2724682Lithium diisopropylamideHCID 19008991HCID 19008991, compound

Product 1

HCID 19008982HCID 19008982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 0.308 g. of picoline in 20 mL of tetrahydrofuran, which was cooled to -78° C., was added 1.6 mL of lithium diisopropyl amide, and the mixture was stirred at -78° C. for 30 minutes. The mixture was then allowed to warm to -10° C. for 2 hours, then cooled again to -78° C. There was then added a solution of 1.0 g. of 1-(4-chlorophenoxy)-4-(2-bromoethyl)benzene in 20 mL of tetrahydrofuran. This mixture was stirred for 30 minutes at -78° C., then allowed to warm to room temperature and stirred overnight. 50 mL of water was added dropwise and the tetrahydrofuran was removed by reducing pressure. The residue was extracted with ethyl acetate, which was concentrated to dryness. The product was purified by HPLC (silica gel 70% pentane; 30% ethyl acetate over 180 minutes) to give 0. 107 g. of an oil.

Workup

  1. temperatureto warm to -10° C. for 2 hours
  2. temperaturecooled again to -78° C
  3. additionThere was then added a solution of 1.0 g
  4. stirringThis mixture was stirred for 30 minutes at -78° C.
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. customthe tetrahydrofuran was removed
  8. extractionThe residue was extracted with ethyl acetate, which
  9. concentrationwas concentrated to dryness
  10. customThe product was purified by HPLC (silica gel 70% pentane; 30% ethyl acetate over 180 minutes)
  11. customto give 0

Sources & evidence

ORD record
ord-39075c8545874cd299b7a91646321aa3
Source dataset
uspto-grants-1994_08
Patent number
US05338742

Reaction notes

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