Carbon Tetrachloride → HCID 86714056, compound

HRID 576347Notes

Reaction equation

HRID 576347 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]2[C@H:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@@H:16]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@@H:14]([CH2:42][O:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[O:13]2)=[CH:10][C:9]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH3:60])=[CH:54][CH:53]=2)=[C:8]([Cl:61])[C:3]=1[O:4][CH2:5]CO.[C:62]([Cl:66])(Cl)(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(#N)C>[CH2:35]([O:34][C@H:15]1[C@H:16]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@@H:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:12]([C:11]2[CH:10]=[C:9]([CH2:51][C:52]3[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH3:60])=[CH:56][CH:57]=3)[C:8]([Cl:61])=[C:3]([O:4][CH2:5][CH2:62][Cl:66])[C:2]=2[Br:1])[O:13][C@@H:14]1[CH2:42][O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 86714055HCID 86714055, compound

Product 1

HCID 86714056HCID 86714056, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of alcohol 79 (2.68 g, 2.95 mmol) in acetonitrile (30 mL) were added CCl4 (3.4 mL, 35.41 mmol) and PPh3 (1.9 g, 7.38 mmol) at 0° C. The mixture was stirred at 55° C. for 3 hours. The mixture was filtrated and concentrated in vacuo. The resultant was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 80 (2.59 g, 95%).

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated in vacuo
  3. customThe resultant was partitioned between EtOAc and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38e29e7f6d3d4069935d06b7bbd852f3
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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