Propylene Oxide → alpha-Methyl-2-furanethanol

HRID 900437Notes

Reaction equation

HRID 900437 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[CH2:11]1[O:14][CH:12]1[CH3:13]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:11][CH:12]([OH:14])[CH3:13]

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 8029FuranHCID 178418339Butyllithium

Product 1

HCID 10855456alpha-Methyl-2-furanethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of furan (7.93 g) in tetrahydrofuran (100 ml) cooled to 5° C. was added dropwise n-butyl lithium (80.2 ml, 1.6M in hexanes). The mixture was stirred for 2 h. A solution of propylene oxide (12.2 ml) was added dropwise and the resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with saturated ammonium chloride and extracted with diethyl ether. The organics were dried (MgSO4) and concentrated. The crude oil was distilled to give 1-(2-furyl)-propan-2-ol (3.85 g, b.p. 68-70° C. at 6.0 mm).

Workup

  1. stirringthe resulting mixture was stirred at 0° C. for 1 h
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with diethyl ether
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. distillationThe crude oil was distilled

Sources & evidence

ORD record
ord-d72e89fe53f54547a35b54881864a80b
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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