Boron Trichloride → HCID 19350796, compound

HRID 1636293Notes

Reaction equation

HRID 1636293 reaction equation
[Cl:1][C:2]1[C:3](=[O:24])[NH:4][C:5](=[O:23])[N:6]([CH:8]2[CH2:13][S:12][CH:11]([CH2:14][O:15]CC3C=CC=CC=3)[CH2:10][O:9]2)[CH:7]=1.B(Cl)(Cl)Cl.CO.C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:24])[NH:4][C:5](=[O:23])[N:6]([CH:8]2[CH2:13][S:12][CH:11]([CH2:14][OH:15])[CH2:10][O:9]2)[CH:7]=1

Participants

6

Reactant 4

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 19350814HCID 19350814, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 19350796HCID 19350796, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-Chloro-1-(5-benzyloxymethyl-1,4-oxathian-2-yl) uracil (0.42 g) was dissolved in methylene chloride (40 ml), and the solution cooled to -78° C. To the solution, 3M boron trichloride (11.5 ml) was added dropwise, and the mixture stirred at the same temperature for 4 hours. After adding a mixed solution of methanol-methylene chloride (1/1, 14 ml) at room temperature, sodium bicarbonate was added thereto. Upon stirring and filtering the mixture, the filtrate was concentrated under reduced pressure, and the residue was purified on a silica gel column (eluent: chloroform/methanol=10/1) to obtain the desired product (0.06 g) as white solid.

Workup

  1. stirringUpon stirring
  2. filtrationfiltering the mixture
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue was purified on a silica gel column (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-34f05d58db0f4735b1412be6c17256e7
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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