Methanol → 2,5-Dihydro-2,5-dimethoxy-2-(3-butynyl)furan

HRID 1032503Notes

Reaction equation

HRID 1032503 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]#[CH:9].[C:10](=[O:13])([O-])[O-].[Na+].[Na+].BrBr.[CH3:18][OH:19]>>[CH3:18][O:19][C:2]1([CH2:6][CH2:7][C:8]#[CH:9])[CH:3]=[CH:4][CH:5]([O:13][CH3:10])[O:1]1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 10340Sodium CarbonateHCID 24408BromineHCID 221661432-(But-3-yn-1-yl)furan

Product 1

HCID 147744262,5-Dihydro-2,5-dimethoxy-2-(3-butynyl)furan

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of 6.01 g of 4-(2-furyl)-1-butyne [Perfumery Essent. Oil Record., 57, 364 (1966)], 10.6 g of sodium carbonate and 150 ml of methanol at -25° C., was added dropwise a solution of 8.0 g of bromine in 50 ml of methanol during a period of 3 hours. The mixture was then stirred at 25° C. for 45 minutes and concentrated in vacuo. The residue was partitioned with ether and brine. The ether layer was separated, washed with brine, dried and concentrated. Distillation of the residue at 0.5mm gave 6.62 g of the desired compound as a light yellow liquid, bp 57°-61° C. (0.5 mm).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned with ether and brine
  3. customThe ether layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. distillationDistillation of the residue at 0.5mm

Sources & evidence

ORD record
ord-faaebcb1db3b402a8c26a27389d80a9d
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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