Triethylamine → 2-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)furan

HRID 566391Notes

Reaction equation

HRID 566391 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=O.C(N([CH2:15][CH3:16])CC)C.CC[O:19][CH2:20]C.C[C:23](C)=[O:24]>ClCCl.B(F)(F)F.CCOCC>[CH3:3][C:4]12[CH2:20][O:19][C:2]([C:6]3[O:8][CH:9]=[CH:15][CH:16]=3)([O:24][CH2:23]1)[O:1][CH2:5]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11902Methyl 2-furoateHCID 21584533Acetone diethylether

Product 1

HCID 226097422-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)furanYield 19%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Methyl-3-oxetane)methyl 2-furoate (11.8 g, 60.1 mmol) was dissolved in dichloromethane (250 ml) and the solution was cooled to 0° C. Boron trifluoride-etherate (10 drops) was added and the mixture stirred at room temperature, and then left to stand for two months. Triethylamine (0.5 ml, 0.36 g, 3.6 mmol) was added and the mixture concentrated to give a sticky white solid. Trituration with ether/acetone gave the title compound as a white solid (2.2 g, 11.2 mmol, 19%); δH [2H6]DMSO 8.00 (1H,s), 7.34 (1H,d), 7.71 (1H,dd), 4.44 (2H,d), 4.35 (2H,s), 4.28 (2H,d), 1.31 (3H,s).

Workup

  1. waitleft
  2. waitto stand for two months
  3. concentrationthe mixture concentrated
  4. customto give a sticky white solid

Sources & evidence

ORD record
ord-8d02cbee79744e85842cad181eaba12c
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

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