Carbon Tetrachloride → HCID 10635636, compound

HRID 1033100Notes

Reaction equation

HRID 1033100 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:18]O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)(Cl)[Cl:21].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[C:9]([CH2:18][Cl:21])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 10634423HCID 10634423, compound

Product 1

HCID 10635636HCID 10635636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the alcohol from Step 1 (1.46 g, 5.8 mmoL) in CH2Cl2 (50 mL) was added CCl4 (5.7 mL, 58 mmoL, 10 eq.) followed by Ph3P (3 g, 11.7 mmoL, 2 eq.). The resulting mixture was refluxed for 2 hr. The solvent was evaporated and a purification by flash chromatography on silica gel (hexanes: EtOAc; 8:2) gave the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hr
  2. customThe solvent was evaporated
  3. customa purification by flash chromatography on silica gel (hexanes: EtOAc; 8:2)

Sources & evidence

ORD record
ord-6902cedf2f47422c94d2fcc98ecf6a7e
Source dataset
uspto-grants-1994_05
Patent number
US05308852

Reaction notes

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