Carbon Tetrachloride → HCID 86714034, compound
Reaction equation
[Br:1][C:2]1[C:11]([Cl:12])=[C:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH3:21])=[CH:16][CH:15]=2)[CH:9]=[C:8]([CH:22]2[C@H:27]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@@H:26]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@H:25]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@@H:24]([CH2:52][O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[O:23]2)[C:3]=1[O:4][CH2:5]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:80]([Cl:84])(Cl)(Cl)Cl>>[CH2:45]([O:44][C@H:25]1[C@H:26]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:22]([C:8]2[CH:9]=[C:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH3:21])=[CH:18][CH:19]=3)[C:11]([Cl:12])=[C:2]([Br:1])[C:3]=2[O:4][CH2:5][CH2:80][Cl:84])[O:23][C@@H:24]1[CH2:52][O:53][CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1Participants
4
Conditions
- Temperature
- 55 °C
Procedure
To a solution of the intermediate 33 (3.04 g, 3.41 mmol) were added triphenylphosphine (2.23 g, 8.52 mmol) and CCl4 (3.7 mL). After stirring for 2 h at 55° C., the solvent was evaporated off. The residue was dissolved in EtOAc (100 mL), washed with saturated NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 34 (1.62 g, 1.78 mmol, 52%).
Workup
- customthe solvent was evaporated off
- dissolutionThe residue was dissolved in EtOAc (100 mL)
- washwashed with saturated NaHCO3 solution
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-b60aa6adcb9c45b6a9a1893418639de5
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371303B2
Reaction notes
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