Aluminum(III) Chloride → HCID 21569002, compound

HRID 1579644Notes

Reaction equation

HRID 1579644 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][C:12]1[O:16][C:15]([C:17]([CH:20]2[CH2:24][CH2:23][C:22]([CH3:27])([CH:25]=[CH2:26])[O:21]2)(O)[CH3:18])=[CH:14][CH:13]=1>C(OCC)C>[CH3:11][C:12]1[O:16][C:15]([CH:17]([CH:20]2[CH2:24][CH2:23][C:22]([CH3:27])([CH:25]=[CH2:26])[O:21]2)[CH3:18])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 21569003HCID 21569003, compound

Product 1

HCID 21569002HCID 21569002, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

52.5 g of aluminum trichloride were progressively added to 200 ml of anhydrous diethyl ether, followed by 7.5 g of lithium-aluminum hydride. The above mixture was then cooled to 0° and 35 g of crude 1-(5-methyl-fur-2-yl)-1-(5-methyl-5-vinyl-tetrahydrofur-2-yl)-ethanol -- see letter (a) -- were then added dropwise, under vigourous stirring. 30 min. after addition of the reactants, the obtained mixture was poured onto crushed ice and the organic layer extracted with ether, washed with a saturated aqueous solution of NaHCO3, then dried and evaporated in accordance with the usual techniques, to afford 28.9 g of raw material. The thus obtained residue was finally purified by means of a column chromatography (Silicagel - hexane/ether 9:1) followed by a fractional distillation, b.p. 49°-51°/0.001 Torr, of the eluate. 14.7 g (54%) of 1-(5-methyl-fur-2-yl)-1-(5-methyl-5-vinyl-tetra-hydrofur-2-yl-)-ethane were thus isolated, as a mixture of 4 isomers according to a vapor phase chromatography analysis (CARBOWAX 20 M - 5m -- ca. 200°C.

Workup

  1. temperatureThe above mixture was then cooled to 0°
  2. additionwere then added dropwise, under vigourous stirring
  3. addition30 min. after addition of the reactants
  4. additionthe obtained mixture was poured
  5. customonto crushed ice
  6. extractionthe organic layer extracted with ether
  7. washwashed with a saturated aqueous solution of NaHCO3
  8. customdried
  9. customevaporated in accordance with the usual techniques
  10. customto afford 28.9 g of raw material
  11. customThe thus obtained residue was finally purified by means of a column chromatography (Silicagel - hexane/ether 9:1)
  12. distillationfollowed by a fractional distillation, b.p. 49°-51°/0.001 Torr

Sources & evidence

ORD record
ord-61bc7f7099e2485fa4dd6f899acf3c9d
Source dataset
uspto-grants-1976_01
Patent number
US03931250

Reaction notes

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