Boron trifluoride etherate → HCID 66691356, compound

HRID 1469191Notes

Reaction equation

HRID 1469191 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[S:42][C:43]([Cl:58])=[C:44]([CH2:46][O:47][Si:48]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[CH:49]([CH3:51])[CH3:50])[CH:45]=1)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>[Cl:58][C:43]1[S:42][C:41]([CH:10]2[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:13]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[O:11]2)=[CH:45][C:44]=1[CH2:46][O:47][Si:48]([CH:55]([CH3:56])[CH3:57])([CH:49]([CH3:50])[CH3:51])[CH:52]([CH3:53])[CH3:54]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66693478HCID 66693478, compound

Product 1

HCID 66691356HCID 66691356, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of alcohol 33 (8.53 g, 10.1 mmol) in CH2Cl2 (50 mL) were added triethylsilane (3.3 mL, 20.2 mmol) and boron trifluoride diethyl etherate (2.6 mL, 20.2 mmol) at −60° C. The mixture was allowed to slowly warm to −20° C. To a mixture was added aq. saturated K2CO3 solution (50 mL) to quench the reaction. The mixture was evaporated under reduced pressure to remove CH2Cl2 and extracted with EtOAc (100 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to yield the title compound 34 (8.22 g), which was carried on to the next step without further purification.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe mixture was evaporated under reduced pressure
  4. customto remove CH2Cl2
  5. extractionextracted with EtOAc (100 mL)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f7e4cc0c0e74962bb2492a2ac619190
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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