Hexane → HCID 10464590, compound

HRID 1451313Notes

Reaction equation

HRID 1451313 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.CCCCCC.[Cl-].[NH4+].CO[CH2:16][CH2:17][O:18][CH3:19].[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1.CN1C(=O)N(C)CCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC.O>[O:23]1[CH:24]=[CH:20][C:21]([C:2]([C:3]2[CH:16]=[CH:17][O:18][CH:19]=2)=[CH2:1])=[CH:22]1

Participants

8

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 86749955HCID 86749955, compoundHCID 178418339Butyllithium

Product 1

HCID 10464590HCID 10464590, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of methyltriphenylphosphonium bromide (145 g; 0.405 mol, dried at 60° C.) in 1 L of ether was added at -20° C. n-butyllithium in hexane (2.5M, 162 ml; 0.405 mol) and the mixture was allowed to stir at room temperature for 1 h. To the above mixture was added 60 g (0.37 mol) of 1,1-di(3-furyl)ketone in 450 ml of DME/THF/DMPU (2:2:0.5) in 10 minutes and the mixture was stirred at room temperature for 1 h.. To the above reaction mixture was added saturated ammonium chloride solution (250 ml), and the mixture was diluted with 500 ml of water. The organic layer was separated, washed with water (2×500 ml), dried, and concentrated in vacuo. The residue was purified by chromatography on silica (hexane, then 10% ether/hexane) to afford 51 g (86%) of 1,1-di(3-furyl)ethylene (Formula III: R2 =R3 =H; R4 =R5 =3-furanyl). This product was further distilled (b.p. 60°-63° C./0.01 mm).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h.
  2. customThe organic layer was separated
  3. washwashed with water (2×500 ml)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica (hexane

Sources & evidence

ORD record
ord-3281f59934dd4f8297985e25f050a3db
Source dataset
uspto-grants-1997_02
Patent number
US05604224

Reaction notes

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