tert-Butanol → 2,2-Dimethyl-1-(pyrazin-2-yl)cyclopropanol

HRID 717596Notes

Reaction equation

HRID 717596 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][C:4]([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)=[O:5].C(O)(C)(C)C>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[CH2:3][C:4]1([C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1)[OH:5]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 5566921-Butanone, 3-methyl-1-pyrazinyl-

Product 1

HCID 157340522,2-Dimethyl-1-(pyrazin-2-yl)cyclopropanol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-methyl-1-(pyrazin-2-yl)butan-1-one (1.0 g, 6.1 mmol) in 120 mL of a 19/1 mixture of tert-butanol and benzene was irradiated using a 6 W 366 nm lamp (TLC lamp) in a pyrex glass tube. The conversion was 50% after 16 h and 80% after 40 h. At this point the volatiles were removed in vacuo and the material was purified by column chromatography (silica, EtOAc/heptanes 1/4) to afford 2,2-dimethyl-1-(pyrazin-2-yl)cyclopropanol as a reddish-brown oil (375 mg; 38%). 1H NMR (CDCl3) 0.90 (3H, s), 1.00 (2H, d), 1.40 (2H, s), 3.20 (1H, s), 8.42 (1H, m), 8.50 (1H, m), 8.76 (1H, m).

Workup

  1. customwas irradiated
  2. customafter 16 h
  3. customAt this point the volatiles were removed in vacuo
  4. customthe material was purified by column chromatography (silica, EtOAc/heptanes 1/4)

Sources & evidence

ORD record
ord-568abda6df2040718dbc8fdae84db6e4
Source dataset
uspto-grants-2015_11
Patent number
US09193722B2

Reaction notes

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