Boron Trichloride → HCID 178430073, compound

HRID 1636292Notes

Reaction equation

HRID 1636292 reaction equation
C(OC[CH:10]1[CH2:15][O:14][CH:13]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:12][S:11]1)C1C=CC=CC=1.B(Cl)(Cl)Cl.[CH3:29][OH:30].C(Cl)Cl>C(Cl)Cl>[OH:30][CH2:29][SH:11]1[CH2:10][CH2:15][O:14][CH:13]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:12]1

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 19350815HCID 19350815, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 178430073HCID 178430073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-(5-Benzyloxymethyl-1,4-oxathian-2-yl)thymine (0.14 g) was dissolved in methylene chloride (10 ml), and the solution cooled to -78° C. To the solution, 1M boron trichloride (4.1 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, 8 ml), the temperature of the reaction mixture was raised to room temperature. Upon concentrating the reaction mixture under reduced pressure, the resultant dark brown oil was purified on a silica gel column (eluent: chloroform/methanol=20/1) to obtain the desired product (0.07 g) as pale yellow solid.

Workup

  1. temperaturethe temperature of the reaction mixture was raised to room temperature
  2. concentrationUpon concentrating the reaction mixture under reduced pressure
  3. customthe resultant dark brown oil was purified on a silica gel column (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-05c1422258b14a46926ceacff73239b7
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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