Boron trifluoride etherate → 5-(Hydroxymethyl)-3-(2-propyn-1-yl)-2(3H)-thiazolone

HRID 1650743Notes

Reaction equation

HRID 1650743 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]#[CH:9])[CH:5]=[C:4]([C:10](OCC)=[O:11])[S:3]1.B(F)(F)F.CCOCC.[H-].C([Al+]CC(C)C)C(C)C.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[CH:5]=[C:4]([CH2:10][OH:11])[S:3][C:2]1=[O:1])[C:8]#[CH:9]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5462222PotassiumHCID 14457166HCID 14457166, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 144571625-(Hydroxymethyl)-3-(2-propyn-1-yl)-2(3H)-thiazoloneYield 34.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 8.44 g of the product of Step B in 100 ml of toluene was cooled to -65° C. to -70° C. and 5.6 g of boron trifluoride etherate were added. The mixture was stirred for 30 minutes and 200 ml of a 1.2M solution of diisobutyl aluminium hydride in toluene were introduced over 2 hours 15 minutes. Stirring was carried out for a further 30 minutes and the mixture was poured into 1.5 l of a M solution of potassium and sodium tartrate. After stirring for one hour and decanting, extraction was carried out with ethyl acetate. The extracts were washed with water saturated with sodium chloride, dried and brought to dryness. The residue was chromatographed and elution with a hexane-chloroform-acetone mixture (6-2-2) yielded. 2.33 g of the expected product melting at 97° to 98° C.

Workup

  1. stirringStirring
  2. waitwas carried out for a further 30 minutes
  3. stirringAfter stirring for one hour
  4. customdecanting
  5. extractionextraction
  6. washThe extracts were washed with water saturated with sodium chloride
  7. customdried
  8. customThe residue was chromatographed
  9. washelution with a hexane-chloroform-acetone mixture (6-2-2)
  10. customyielded

Sources & evidence

ORD record
ord-28902628b5804573891c929cf6b642b6
Source dataset
uspto-grants-1990_05
Patent number
US04925862

Reaction notes

Loading…