1-Butanol → HCID 15407953, compound

HRID 1107510Notes

Reaction equation

HRID 1107510 reaction equation
C[N+]1([O-])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[OH2:9].[CH2:10]([OH:14])[CH2:11]CC.CC1OC2[C:25]([CH:26]=[CH2:27])=[CH:24][CH:23]=[CH:22]C=2C=1C>CC(C)=O.[Os](=O)(=O)(=O)=O>[CH3:3][C:4]1[O:5][C:6]2[C:7]([CH:10]([OH:14])[CH2:11][OH:9])=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]=1[CH3:27]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 962Water2×HCID 82029Methyl morpholine oxideHCID 15407951HCID 15407951, compound

Product 1

HCID 15407953HCID 15407953, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent2×

Procedure

3.86 g (28.6 mmol) of N-methylmorpholine N-oxide, 10 ml of water and 20 ml of acetone are placed in a 100 ml three-necked flask. 2.1 ml of a 1% by mass solution of osmium tetroxide in tort-butanol are added dropwise, followed by a solution of 5.2 g (26 mol) of 2,3-dimethyl-7-ethenylbenzofuran in 10 ml of acetone. The reaction mixture is stirred for 5 hours at room temperature. 100 ml of water are added and extraction is carried out with ethyl acetate (3×150 ml). The organic phases are combined, washed with 100 ml of a 1% sodium bisulphite solution and 100 ml of a 1% sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solvent: 35% ethyl acetate in cyclohexane). 4.2 g (Yield: 85%) of 2,3-dimethyl-7-(1,2-dihydroxyethyl)benzofuran are obtained in the form of a white solid. M.p.=93-95° C.

Workup

  1. extractionextraction
  2. washwashed with 100 ml of a 1% sodium bisulphite solution and 100 ml of a 1% sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on a silica column (elution solvent: 35% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-2150191620d8429bb6f4f4bed13c2742
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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