Boron trifluoride etherate → HCID 10899662, compound

HRID 1379285Notes

Reaction equation

HRID 1379285 reaction equation
B(F)(F)F.CCOCC.[OH:10][CH:11]1[CH2:15][CH2:14][O:13][C:12]1=[O:16].[C:17]([N:21]=[C:22]=[O:23])([CH3:20])([CH3:19])[CH3:18].C(=O)(O)[O-].[Na+]>ClCCl.[Cl-].[Na+].O>[C:17]([NH:21][C:22]([O:10][CH:11]1[CH2:15][CH2:14][O:13][C:12]1=[O:16])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 62412tert-Butyl isocyanateHCID 516892Sodium BicarbonateHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 10899662HCID 10899662, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Boron trifluoride diethyl etherate (1.38 g) was added dropwise, over a period of fifteen minutes, to a stirred solution of 3-hydroxytetrahydrofuran-2-one (10.0 g) and t-butylisocyanate (9.7 g) in dry dichloromethane (300 ml), whilst maintaining the temperature below 10° C. The mixture was stirred at room temperature for a further four hours, treated with brine and sufficient aqueous sodium bicarbonate solution to render the aqueous phase basic, then extracted several times with dichloromethane. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure to give the title compound (18.5 g, m.p. 104°-106° C.). NMR (CDCl3): δ 1.34(9H,s); 2.28(1H,m); 2.73(1H,m); 4.28(1H,dt); 4.46(1H,dt); 4.90(1H,bs); 5.31(1H,t). MS: M+ 201. The addition can also be catalysed using triethylamine or aqueous hydrogen chloride in place of boron trifluoride. However a rearrangement product can be formed in variable amounts which can necessitate purification of the desired material, for example by chromatography on silica using hexane-ethyl acetate (3:1) as eluant.

Workup

  1. temperaturewhilst maintaining the temperature below 10° C
  2. extractionextracted several times with dichloromethane
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cdb6986590af4fcd9b50b9fb887eeb77
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

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