Tetrahydrofuran → 1-Benzylcyclopentanol

HRID 1180728Notes

Reaction equation

HRID 1180728 reaction equation
[C:1]1(=[O:5])[CH2:4][CH2:3][CH2:2]1.[CH2:6]([Mg]Cl)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O1CCC[CH2:16]1>>[CH2:6]([C:1]1([OH:5])[CH2:4][CH2:3][CH2:2][CH2:16]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 14496CyclobutanoneHCID 178418336HCID 178418336, compound

Product 1

HCID 5642421-BenzylcyclopentanolYield 53%

Procedure

To 2.85 g (33.88 mmol) of cyclobutanone in 170 mL of tetrahydrofuran at 0° C. was added 25.41 mL (50.82 mmol) of a 2 M solution of benzyl magnesium chloride in tetrahydrofuran and the mixture was allowed to warm to RT and stirred for 17 h. The reaction was quenched with ice, then acidified with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:6) to give 3.14 g (53%) of 1-benzylcyclopentanol. 1H NMR (300 MHz, DMSO-d6) δ 7.27-7.19 (m, 5H), 4.19 (s, 1H), 2.78 (s, 2H), 1.69 (br m, 2H), 1.51 (br m, 6H); ES-LCMS m/z 176 (M+H).

Workup

  1. customThe reaction was quenched with ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-ce0b5e6577294b00b5a91d7826e477ad
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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