Boron trifluoride etherate → HCID 86714019, compound

HRID 2206676Notes

Reaction equation

HRID 2206676 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]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C:10]1([C:41]1[CH:49]=[C:48]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][CH:52]=2)[C:47]([Br:59])=[C:46]2[C:42]=1[CH2:43][CH2:44][CH2:45]2)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:24]([O:23][C@H:13]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]([C:41]2[CH:49]=[C:48]([CH2:50][C:51]3[CH:52]=[CH:53][C:54]([O:57][CH3:58])=[CH:55][CH:56]=3)[C:47]([Br:59])=[C:46]3[C:42]=2[CH2:43][CH2:44][CH2:45]3)[O:11][C@@H:12]1[CH2:31][O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 86714018HCID 86714018, compound

Product 1

HCID 86714019HCID 86714019, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of the intermediate 16 (6.96 g, 8.13 mmol) in CH2Cl2 (40.1 mL) were added triethylsilane (3.24 mL, 16.2 mmol) and boron trifluoride diethyl etherate (2.55 mL, 16.2 mmol) at −60° C. under nitrogen atmosphere. The mixture was warmed up to −30° C. for 3 h. To the mixture was added saturated K2CO3 solution (50 mL) slowly and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired intermediate 17 (2.87 g, 3.42 mmol, 42%).

Workup

  1. extractionthe mixture was extracted with EtOAc (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7eee103a4be482ba039cfef48232332
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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