Tetrahydrofuran → HCID 21288122, compound

HRID 868283Notes

Reaction equation

HRID 868283 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:9][C:10]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=CC=1C=O)CO.[O:20]1CCC[CH2:21]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:3]([C:2]1[CH:1]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:10]=1[O:9][CH2:6][O:20][CH3:21])=[CH2:4]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 20095549HCID 20095549, compoundHCID 178418339Butyllithium

Product 1

HCID 21288122HCID 21288122, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a suspension of 104 g (0.291 moles) of methyltriphenylphosphonium bromide in 100 ml dry tetrahydrofuran at 0° was added 115 ml (0.275 moles) of 2.4M n-butyllithium and the dark red solution was stirred at 0° for 30 minutes. Then a solution of 38.2 g (0.195 moles) of 2-(3-oxapropyloxy)-5-methoxybenzaldehyde in 100 ml of dry tetrahydrofuran was added and the solution was stirred at room temperature for 60 minutes. The solution was concentrated and the residue partitioned between ether and water. The ether layer was washed with aqueous Na2CO3, then brine, then dried (Na2SO4) and concentrated. The oily residue was dissolved in 500 ml of 10% ethylacetate-hexane and cooled at 0° overnight, then filtered. The filtrate was concentrated to give 33.8 g (89%) of 2-ethenyl-4-methoxy-1-O-methoxymethylphenol as a pale yellow liquid. NMR (CDCl3) δ3.45 (s, 3H), 3.71 (s, 3H), 5.10 (s, 2H), 5.20 (d of d, 1H), 5.6 (d of d, 1H), 6.5-7.0 (m, 4H).

Workup

  1. stirringthe solution was stirred at room temperature for 60 minutes
  2. concentrationThe solution was concentrated
  3. customthe residue partitioned between ether and water
  4. washThe ether layer was washed with aqueous Na2CO3
  5. dry with materialbrine, then dried (Na2SO4)
  6. concentrationconcentrated
  7. dissolutionThe oily residue was dissolved in 500 ml of 10% ethylacetate-hexane
  8. temperaturecooled at 0° overnight
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9dd5101eaea347729c84d4851e91edd8
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

Loading…