Phenethyl bromide → HCID 22618832, compound

HRID 635480Notes

Reaction equation

HRID 635480 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=[O:22])[CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH2:29][CH2:30][Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(CCBr)C=CC=CC=1.[Mg].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:30][CH2:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:22])[CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 7666Phenethyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 226187871,5-Bis(benzyloxy)pentan-3-oneHCID 178419670HCID 178419670, compound

Product 1

HCID 22618832HCID 22618832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,5-dibenzyloxy-3-pentanone (13.9 g) in tetrahydrofuran (150 ml) was dropwise added a solution of 2-phenylethyl-magnesium bromide, which was prepared from 2-phenylethyl bromide (24 g) and magnesium (3.1 g), in tetrahydrofuran (100 ml) under ice-cooling. The mixture was stirred under ice-cooling for 90 minutes, poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue obtained was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1) to give the subject compound (8.1 g) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling for 90 minutes
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b020010bbda0458ab007c5cab772613e
Source dataset
uspto-grants-2001_02
Patent number
US06187821B1

Reaction notes

Loading…