Boron trifluoride → HCID 20061618, compound

HRID 1085206Notes

Reaction equation

HRID 1085206 reaction equation
B(F)(F)F.[O:5]=[C:6]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]([C:14]([F:17])([F:16])[F:15])=[C:8]([C:18](OCC)=[O:19])[S:7]1.[H-].C([Al+]CC(C)C)C(C)C.[Na].[K]>C1(C)C=CC=CC=1>[OH:19][CH2:18][C:8]1[S:7][C:6](=[O:5])[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]=1[C:14]([F:16])([F:17])[F:15]

Participants

7

Reactant 5

HCID 6356Boron trifluorideHCID 5360545SodiumHCID 5462222PotassiumHCID 20061622HCID 20061622, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20061618HCID 20061618, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-65 °C

Procedure

4.3 ml of boron trifluoride ethereate were introduced at -65° C. into a solution of 8.65 g of the product of Step A in 100 ml of toluene and the mixture was stirred at -65° C. Then, 155 ml of 0.5M solution of diisobutylaluminium hydride in toluene were introduced and the mixture was poured into an iced molar solution of sodium and potassium double tartrate followed by stirring for 2 hours. After decanting and extraction with ethyl acetate, the extracts were washed with water and with a saturated solution of sodium chloride, dried, filtered and concentrated. The residue was chromatographed on silica and elution with a hexane-ethyl acetate mixture (7-3) yielded 4 g of the expected product with a Rf=0.25.

Workup

  1. stirringby stirring for 2 hours
  2. customAfter decanting
  3. extractionextraction with ethyl acetate
  4. washthe extracts were washed with water and with a saturated solution of sodium chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica and elution with a hexane-ethyl acetate mixture (7-3)

Sources & evidence

ORD record
ord-c0afe71bec8e4feebdce4955868ca675
Source dataset
uspto-grants-1991_04
Patent number
US05008281

Reaction notes

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