Boron trifluoride etherate → HCID 20061642, compound

HRID 1650745Notes

Reaction equation

HRID 1650745 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([C:14]([F:17])([F:16])[F:15])=[C:4]([C:18](OCC)=[O:19])[S:3]1.B(F)(F)F.CCOCC.[H-].C([Al+]CC(C)C)C(C)C.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[C:5]([C:14]([F:17])([F:16])[F:15])=[C:4]([CH2:18][OH:19])[S:3][C:2]1=[O:1])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 5360545SodiumHCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 21225700DiisobutylaluminumhydrideHCID 53945212HCID 53945212, compound

Product 1

HCID 20061642HCID 20061642, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.13 g of the product of Step A, 30 ml of toluene and 1.3 ml of boron trifluoride etherate were stirred for 30 minutes at -65° to -70° C. and 48 ml of 1.2M solution of diisobutyl aluminium hydride in toluene were added over 2 hours. The mixture was poured into an iced molar solution of sodium and potassium tartrate and after stirring for one hour and decanting, extraction was carried out with ethyl acetate. The extracts were washed, dried and brought to dryness and the residue was chromatographed on silica. Elution with a hexaneisopropyl ether mixture (1-1) yielded 2.16 g of the expected product with a Rf=0.1.

Workup

  1. customdecanting
  2. extractionextraction
  3. washThe extracts were washed
  4. customdried
  5. customthe residue was chromatographed on silica
  6. washElution with a hexaneisopropyl ether mixture (1-1)

Sources & evidence

ORD record
ord-39ef2fbbe36b4dd596e40bc2c7a42bfc
Source dataset
uspto-grants-1990_05
Patent number
US04925862

Reaction notes

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