Hydrochloric Acid → (R)-(+)-2-(2-furyl)-3-methyl-1-butanol

HRID 1655761Notes

Reaction equation

HRID 1655761 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]([CH:16]([CH3:18])[CH3:17])[C:13](O)=[O:14].Cl>CCOCC.O1CCCC1>[O:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C@H:12]([CH:16]([CH3:18])[CH3:17])[CH2:13][OH:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 197908462-(Furan-2-yl)-3-methylbutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22847751(R)-(+)-2-(2-furyl)-3-methyl-1-butanolYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

10.5 g (0.277 mol) of lithium aluminium hydride were suspended in 100 ml of absolute ether and treated while stirring within 10 minutes with 100 ml of absolute tetrahydrofuran. To this stirred suspension was added dropwise within 6-8 hours, while heating to reflux, 46.7 g (0.277 mol) of (+) 2-(2-furyl)-3-methylbutyric acid in 100 ml of absolute tetrahydrofuran. The reaction mixture was cooled and treated slowly with a 3N hydrochloric acid solution. The organic phase was separated, washed with water, dried and evaporated under reduced pressure. The remaining oil was distilled in a high vacuum, to obtain 32 g (75%) of (R)-(+)-2-(2-furyl)-3-methyl-1-butanol as a colorless liquid of 96% purity, boiling point 58°/39 Pa, [α]D20 =+2.5° (c=1%, ethanol).

Workup

  1. additiontreated
  2. additionTo this stirred suspension was added dropwise within 6-8 hours
  3. temperaturewhile heating
  4. temperatureto reflux
  5. temperatureThe reaction mixture was cooled
  6. customThe organic phase was separated
  7. washwashed with water
  8. customdried
  9. customevaporated under reduced pressure
  10. distillationThe remaining oil was distilled in a high vacuum

Sources & evidence

ORD record
ord-abea6673995d4b5aad664fae5fb317e1
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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