Cyclohexyl bromide → HCID 20380992, compound

HRID 1447980Notes

Reaction equation

HRID 1447980 reaction equation
[C:1]([CH:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Mg].[Cl-].[NH4+].[O:25]1CCCC1>>[OH:25][C:2]1([CH:1]([CH:9]2[CH2:13][O:12][C:11](=[O:14])[NH:10]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 5

HCID 7960Cyclohexyl bromideHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20380987HCID 20380987, compound

Product 1

HCID 20380992HCID 20380992, compound

Procedure

5.0 g (0.0262 mole) of 4-benzoyl oxazolidin-2-one dissolved in 100 ml of absolute tetrahydrofuran are added dropwise while cooling with ice to a Grignard solution prepared from 12.8 ml (0.127 mole) of bromocyclohexane and 2.98 g (0.128 gram equivalent) of magnesium in 150 ml of absolute tetrahydrofuran. This solution is stirred for 2 hours at 60° C., subsequently hydrolysed with approximately 500 ml of a saturated ammonium chloride solution and repeatedly extracted with chloroform. The organic phases are combined, dried over Na2SO4 and concentrated in a rotary evaporator. The oil is taken up in ether. The crystals formed are filtered off under suction.

Workup

  1. additionare added dropwise
  2. temperaturewhile cooling with ice to a Grignard solution
  3. extractionrepeatedly extracted with chloroform
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in a rotary evaporator
  6. customThe crystals formed
  7. filtrationare filtered off under suction

Sources & evidence

ORD record
ord-2b58e46b684b449fa2dabacd566ede4a
Source dataset
uspto-grants-1979_12
Patent number
US04179442

Reaction notes

Loading…