HCID 15644271, compound → HCID 10039450, compound

HRID 359544Notes

Reaction equation

HRID 359544 reaction equation
[CH:1]1([C:5]([OH:15])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:8])[CH3:7])[CH2:4][CH2:3][CH2:2]1.C1CNC(=O)C1.[Br:22][Br-]Br>O1CCCC1>[Br:22][CH2:7][C:6](=[O:8])[C:5]([CH:1]1[CH2:4][CH2:3][CH2:2]1)([OH:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 15644271HCID 15644271, compound

Product 1

HCID 10039450HCID 10039450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 5-L round bottomed flask equipped with a reflux condenser and an overhead stirrer was placed a solution of 276 3 g (1.35 mole) of 1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone in 3 L of tetrahydrofuran. To this solution was added 903 g (1.82 mole) of pyrrolidone hydrotribromide. The mixture was refluxed for 24 hours and allowed to cool to room temperature. It was partitioned between 4 L of water and 4 L of ether. The organic layer was separated, washed three times with a saturated solution of sodium bicarbonate and once with brine. It was dried over anhydrous magnesium sulfate and the solvent removed. Crystallization of the residue from hexane gave 195 g of 3-bromo-1-cyclobutyl-1-hydroxy-1-phenyl -2-propanone, mp 79°-80° C. NMR (CDCl3) 1.8-2.2 (m, 6 H), 3.4-3.6 (m, 1 H), 3.9-4.1 (m, 2 H), 7.2-7.7 (m, 5 H); IR (KBr) 3471, 2946, 1725, 627 cm-1.

Workup

  1. customIn a 5-L round bottomed flask equipped with a reflux condenser and an overhead stirrer
  2. temperatureThe mixture was refluxed for 24 hours
  3. customIt was partitioned between 4 L of water and 4 L of ether
  4. customThe organic layer was separated
  5. washwashed three times with a saturated solution of sodium bicarbonate
  6. dry with materialIt was dried over anhydrous magnesium sulfate
  7. customthe solvent removed
  8. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-a9a7af97808a4580acb055ce0ff8601b
Source dataset
uspto-grants-1991_03
Patent number
US05001160

Reaction notes

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