Boron trifluoride etherate → HCID 23045064, compound

HRID 2108031Notes

Reaction equation

HRID 2108031 reaction equation
C([Li])CCC.[CH2:6]([O:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]#[CH:8].B(F)(F)F.CCOCC.[O:28]1[CH2:31][CH2:30][CH2:29]1.[Cl-].[NH4+]>C1COCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][CH2:10][O:9][CH2:6][C:7]#[C:8][CH2:31][CH2:30][CH2:29][OH:28]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 10423Oxetane2×HCID 25517Ammonium ChlorideHCID 23045087HCID 23045087, compoundHCID 178418339Butyllithium

Product 1

HCID 23045064HCID 23045064, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.57M in hexane, 35 ml) was added to a stirred solution of 2-[3-[(2-propynyl)oxy]propyl]pyridine (9.0 g) in dry THF (60 ml) at -78° under nitrogen. Boron trifluoride etherate (6.8 ml) was added and the mixture was stirred at -78° for 30 min. Oxetane (10 ml) was added and after 2 h at -78°, the mixture was treated with more oxetane (10 ml). The dark mixture was allowed to warm to 0°, saturated ammonium chloride (100 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The organic layer was washed with brine, dried and concentrated to a dark oil which was purified by FCC eluting with ether to give the title compound as an orange oil (5.1 g), t.l.c. (ethyl acetate-triethylamine 99:1) Rf 0.35.

Workup

  1. temperatureto warm to 0°
  2. extractionthe mixture was extracted with ethyl acetate (2×50 ml)
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated to a dark oil which
  6. customwas purified by FCC
  7. washeluting with ether

Sources & evidence

ORD record
ord-5a5dabc0a24e4b90a0f7fa936c88e26b
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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