Water → HCID 18689385, compound

HRID 1871843Notes

Reaction equation

HRID 1871843 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[C:11]1[C:15]([CH3:17])([CH3:16])[O:14][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=3)=[N:12]1)[CH2:8]2.B(I)(I)I.O>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[C:11]1[C:15]([CH3:17])([CH3:16])[O:14][C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)=[N:12]1)[CH2:8]2

Participants

5

Reactant 3

HCID 962Water2×HCID 83546Borane, triiodo-HCID 18689382HCID 18689382, compound

Product 1

HCID 18689385HCID 18689385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7 mmol 4-adamantylidene-2-(3'-methoxyphenyl)-5,5-dimethyl-oxazoline in 20 ml absolute methylene chloride is added dropwise to a solution of 14 mmol boron triiodide while stirring at -25° C. with the exclusion of air and water. The mixture is heated to room temperature within one hour and stirred for a further 4 h. After admixing with 50 ml water the organic phase is separated and dried over sodium sulfate. The solvent is removed by distillation. The oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:3).

Workup

  1. customis separated
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is removed by distillation
  4. customThe oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:3)

Sources & evidence

ORD record
ord-12c853bd71b7413486a92e4a70faa90d
Source dataset
uspto-grants-2000_08
Patent number
US06107036

Reaction notes

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