HCID 86714056, compound → HCID 86714057, compound

HRID 576348Notes

Reaction equation

HRID 576348 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)[C@H:12]([C:31]2[CH:36]=[C:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=3)[C:34]([Cl:47])=[C:33]([O:48][CH2:49][CH2:50]Cl)[C:32]=2Br)[O:11][C@@H:10]1[CH2:53][O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC>C1COCC1>[Cl:47][C:34]1[C:33]2[O:48][CH2:49][CH2:50][C:32]=2[C:31]([C@H:12]2[C@H:13]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:10]([CH2:53][O:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[O:11]2)=[CH:36][C:35]=1[CH2:37][C:38]1[CH:39]=[CH:40][C:41]([O:44][CH2:45][CH3:46])=[CH:42][CH:43]=1

Participants

4

Reactant 2

HCID 86714056HCID 86714056, compoundHCID 178418339Butyllithium

Product 1

HCID 86714057HCID 86714057, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 80 (2.59 g, 2.79 mmol) in THF (28 mL) was added dropwise n-butyllithium (2.5M in hexane, 2.2 mL, 5.59 mmol) at −78° C. under an atmosphere of nitrogen. The mixture was stirred for 18 hours at −78° C. to 10° C. The mixture was quenched with 1N HCl and extracted with EtOAc. 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 81 (2.0 g, 88%) as brown oil.

Workup

  1. customThe mixture was quenched with 1N HCl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1d030caf22be41de861a572a929251ec
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

Loading…