Tetrahydrofuran → 1-Benzylcyclopentanol

HRID 1180728노트

반응식

HRID 1180728 반응식
[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

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran2회HCID 14496CyclobutanoneHCID 178418336HCID 178418336, 화합물

생성물 1

HCID 5642421-Benzylcyclopentanol수율 53%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ce0b5e6577294b00b5a91d7826e477ad
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282512B2

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