Boron trifluoride etherate → HCID 25017348, compound

HRID 511978Notes

Reaction equation

HRID 511978 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([F:25])(=[O:24])=[O:23])=[CH:11][CH:10]=1)C1C=CC=CC=1.B(F)(F)F.CCOCC>C(S)(S)C.C(OCC)C.O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([F:25])(=[O:24])=[O:23])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 8000Boron trifluoride etherateHCID 25017344HCID 25017344, compound

Product 1

HCID 25017348HCID 25017348, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 336451,1-EthanedithiolSolvent

Procedure

To a solution of 13.1 (0.182 g, 0.5 mmol) in ethanedithiol (10 mL), at room temperature, under an argon atmosphere was added BF3.Et2O (0.282 g, 2.0 mmol). The reaction mixture was stirred at room temperature for 1 hour and then diluted with diethyl ether (20 mL) and water (10 mL). The organic layer was separated and the aqueous phase extracted with diethyl ether. The combined organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue obtained was chromatographed through a column of silica gel eluting with 50% diethyl ether-hexane to give 14.1 (0.096 g, 70% yield) as a white solid (m p 47-51° C.).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase extracted with diethyl ether
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas chromatographed through a column of silica gel eluting with 50% diethyl ether-hexane

Sources & evidence

ORD record
ord-296245e489144a83b3c516ee471c757d
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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