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Boron trifluoride etherate → HCID 70020327, compound

HRID 1357512
Notes
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Reaction equation

HRID 1357512 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[C:5]([O:13][C@H:14]1[C@@H:20]2[C@@H:18]([O:19]2)[CH2:17][C@:16]([OH:25])([C:21]([O:23][CH3:24])=[O:22])[CH2:15]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.B(F)(F)F.CCOCC>C1COCC1.[Cu]I>[C:5]([O:13][C@@H:14]1[CH2:15][C@@:16]([OH:25])([C:21]([O:23][CH3:24])=[O:22])[CH2:17][C@@H:18]([CH:1]=[CH2:2])[C@@H:20]1[OH:19])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 90961573HCID 90961573, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 70020327HCID 70020327, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Vinylmagnesium bromide can be added to a −78° C. suspension of CuI in THF. After stirring for 1 hour, a solution of Example 17D and BF3.Et2O in THF can be added. After stirring for 2 hours at −78° C., the reaction mixture can be quenched with saturated NH4Cl. The reaction mixture can be extracted several times with dichloromethane and the combined dichloromethane layers are washed with brine, dried (MgSO4), filtered and concentrated. The concentrate can be purified by flash column chromatography to afford the desired product.

Workup

  1. stirringAfter stirring for 2 hours at −78° C.
  2. customthe reaction mixture can be quenched with saturated NH4Cl
  3. extractionThe reaction mixture can be extracted several times with dichloromethane
  4. washthe combined dichloromethane layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe concentrate can
  9. custombe purified by flash column chromatography

Sources & evidence

ORD record
ord-41e7395a07e34ce1a282524e4b94a624
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06593314B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes