Water → HCID 136093607, compound

HRID 1871840Notes

Reaction equation

HRID 1871840 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:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=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:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][C:13]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:12]1)[CH2:8]2

Participants

5

Reactant 3

HCID 962Water2×HCID 83546Borane, triiodo-HCID 18689383HCID 18689383, compound

Product 1

HCID 136093607HCID 136093607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6 mmol 4-adamantylidene-2-(4'-methoxyphenyl)-4H-1,3-benzoxazine in 20 ml absolute methylene chloride is added dropwise to a solution of 12 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 hours. 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-5c659b3a32234956bf5e09651599bcd3
Source dataset
uspto-grants-2000_08
Patent number
US06107036

Reaction notes

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