Cyclohexyl bromide → HCID 13565960, compound

HRID 2290820Notes

Reaction equation

HRID 2290820 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH:25]=[O:26])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]1([Mg]Br)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[Mg].C1(Br)CCCCC1>O1CCCC1.CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:23][CH2:24][CH:25]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[OH:26])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7960Cyclohexyl bromideHCID 5462224MagnesiumHCID 20230523HCID 20230523, compoundHCID 178419651HCID 178419651, compound

Product 1

HCID 13565960HCID 13565960, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.4 g of 3-(3,4-dibenzyloxyphenyl)propionaldehyde in 5 ml of anhydrous tetrahydrofuran was cooled to 0° to 5° C. and then 5 ml of an ether solution of cyclohexyl magnesium bromide prepared from 0.12 g of metallic magnesium and 0.82 g of cyclohexyl bromide was added dropwise to the solvent. Thereafter, the reaction mixture was stirred for 15 minutes and after adding thereto 50 ml of an aqueous 5% hydrochloric acid solution, the product was extracted with 30 ml of toluene. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to provide an oily product. The product was applied to silica gel column chromatography and eluted with toluene to provide 0.2 g of 3-(3,4-dibenzyloxyphenyl)-1-cyclohexyl-1-propanol.

Workup

  1. additionwas added dropwise to the solvent
  2. additionafter adding
  3. extraction50 ml of an aqueous 5% hydrochloric acid solution, the product was extracted with 30 ml of toluene
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto provide an oily product
  8. washeluted with toluene

Sources & evidence

ORD record
ord-f14446ee3b884d5ea45dcedf97f3e628
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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