Boron Trichloride → HCID 86685816, compound

HRID 2172721Notes

Reaction equation

HRID 2172721 reaction equation
[N:1]([CH2:4][C@H:5]1[CH:10]=[CH:9][C@H:8]([O:11]CC2C=CC=CC=2)[C@@H:7]([O:19]CC2C=CC=CC=2)[C@@H:6]1[OH:27])=[N+:2]=[N-:3].B(Cl)(Cl)Cl>C(Cl)Cl>[N:1]([CH2:4][C@@H:5]1[C@@H:6]([OH:27])[C@H:7]([OH:19])[C@@H:8]([OH:11])[CH:9]=[CH:10]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 46912125HCID 46912125, compound

Product 1

HCID 86685816HCID 86685816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Azide 11 (103 mg, 0.28 mmol) was dissolved in CH2Cl2 (5 mL) and cooled to −78° C. before BCl3 (5 mL, 1M in CH2Cl2) was added. After 4 h stirring at −78° C., the reaction was quenched by the addition of MeOH. The temperature was raised to room temperature and the solution was concentrated in vacuo. Trace of BCl3 were removed by coevaporating with MeOH. The resulting crude triol 17 was used as such in the click reaction.

Workup

  1. additionwas added
  2. customthe reaction was quenched by the addition of MeOH
  3. temperatureThe temperature was raised to room temperature
  4. concentrationthe solution was concentrated in vacuo
  5. customTrace of BCl3 were removed
  6. customsuch in the click reaction

Sources & evidence

ORD record
ord-597bcb6d3c6a44159fbe1abab4bcc6e1
Source dataset
uspto-grants-2015_06
Patent number
US09056847B2

Reaction notes

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