HCID 86714034, compound → HCID 86714035, compound

HRID 2206691Notes

Reaction equation

HRID 2206691 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]([C:31]2[CH:36]=[C:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][CH:39]=3)[C:34]([Cl:46])=[C:33](Br)[C:32]=2[O:48][CH2:49][CH2:50]Cl)[O:11][C@@H:10]1[CH2:52][O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC>C1COCC1>[Cl:46][C:34]1[C:33]2[CH2:50][CH2:49][O:48][C:32]=2[C:31]([CH:12]2[C@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:10]([CH2:52][O:53][CH2:54][C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[O:11]2)=[CH:36][C:35]=1[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 86714034HCID 86714034, compoundHCID 178418339Butyllithium

Product 1

HCID 86714035HCID 86714035, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the intermediate 34 (1.18 g, 1.30 mmol) in anhydrous THF (15 mL) was added dropwise n-BuLi (2.5 M in hexane, 0.78 mL, 1.94 mmol) at −78° C. under nitrogen atmosphere. The mixture was slowly warmed up to rt and stirred overnight. The reaction mixture was quenched with 1 M HCl solution (10 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide the crude intermediate 35, which was used without further purification (1.03 g, 1.30 mmol, 100%).

Workup

  1. customThe reaction mixture was quenched with 1 M HCl solution (10 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30c731d47c6146eea17d024a01246463
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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