Diiodomethane → HCID 71110625, compound

HRID 2206769Notes

Reaction equation

HRID 2206769 reaction equation
[Zn](CC)[CH2:2]C.C(O)(C(F)(F)F)=O.C(I)I.[C:16]([O:19][C@H:20]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@H:23]([C:34]2[CH:43]=[C:42]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([CH:51]=[CH2:52])=[CH:47][CH:46]=3)[C:41]([Cl:53])=[C:40]3[C:35]=2[CH2:36][CH2:37][CH2:38][O:39]3)[O:22][C@@H:21]1[CH2:54][O:55][C:56](=[O:58])[CH3:57])(=[O:18])[CH3:17]>C(Cl)Cl>[C:16]([O:19][C@H:20]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([O:30][C:31](=[O:33])[CH3:32])[C@H:23]([C:34]2[CH:43]=[C:42]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([CH:51]4[CH2:2][CH2:52]4)=[CH:47][CH:46]=3)[C:41]([Cl:53])=[C:40]3[C:35]=2[CH2:36][CH2:37][CH2:38][O:39]3)[O:22][C@@H:21]1[CH2:54][O:55][C:56](=[O:58])[CH3:57])(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 86714079HCID 86714079, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 71110625HCID 71110625, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The mixture of Et2Zn (1.1 M in toluene, 4 mL, 4.39 mmol) and CH2Cl2 (8 mL) was cooled to 0° C. TFA ((0.34 mL, 4.39 mmol) in CH2Cl2 (4 mL)) was added to the mixture at 0° C. The mixture was stirred at 0° C. for 1 hr. CH2I2 ((0.36 mL, 4.39 mmol) in CH2Cl2 (4 mL)) was added to the mixture at 0° C. The mixture was stirred at 0° C. for 1 hr. The acetate 179 ((270 mg, 0.44 mmol) in CH2Cl2 (4 mL)) was added to the mixture at 0° C. The mixture was warmed up to rt slowly and stirred at room temperature for 15 hours. The mixture was extracted with EtOAc/aq. sat'd NH4Cl (50 mL/50 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified using normal phase column chromatography to provide the title product 180 (152 mg, 55%).

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hr
  2. temperatureThe mixture was warmed up to rt slowly
  3. stirringstirred at room temperature for 15 hours
  4. extractionThe mixture was extracted with EtOAc/aq
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Sources & evidence

ORD record
ord-26cddc8aaabc4cb581c227aa262587a8
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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