Water → HCID 19828139, compound

HRID 1494425Notes

Reaction equation

HRID 1494425 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])C[CH2:9][CH3:10].C([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=O)C.[OH2:27]>C1COCC1>[C:21]1([C:18]2[CH:17]=[CH:16][CH:15]=[CH:20][CH:19]=2)[CH:22]=[CH:23][CH:24]=[C:25]([C:9]([CH3:10])([C:2]2[CH:6]=[CH:5][O:4][CH:3]=2)[OH:27])[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71134-AcetylbiphenylHCID 891643-BromofuranHCID 178418339Butyllithium

Product 1

HCID 19828139HCID 19828139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 14.5 g (0.1 mol) of 3-bromofuran in 500 mL of THF cooled to -78° C. was added dropwise a solution of 64 mL (0.12 mol) to n-butyl lithium in THF. The solution was allowed to stir for 3 hours after the addition was complete, whereupon a solution of 19 g (0.1 mol) 4-acetylbiphenyl in 200 mL of THF was added. The mixture was allowed to stir for 1 hour, then warmed to room temperature. The mixture was then poured into water and extracted with ether (2×500 mL). The ether layers were combined, dried (MgSO4) and concentrated to afford 19.5 g of crude solid. The solid was recrystallized from ether:hexane to afford 12.5 g, 47% of light yellow solid, m.p. 108°-109° C.

Workup

  1. additionafter the addition
  2. additionwas added
  3. stirringto stir for 1 hour
  4. extractionextracted with ether (2×500 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford 19.5 g of crude solid
  8. customThe solid was recrystallized from ether
  9. customhexane to afford 12.5 g, 47% of light yellow solid, m.p. 108°-109° C.

Sources & evidence

ORD record
ord-75e73c8140c345178578e1b05540dd47
Source dataset
uspto-grants-1991_06
Patent number
US05026725

Reaction notes

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