Tetrahydrofuran → 1-Benzylcyclopentanol

HRID 1180728ノート

反応式

HRID 1180728 の反応式
[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

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 14496CyclobutanoneHCID 178418336HCID 178418336、化合物

生成物 1

HCID 5642421-Benzylcyclopentanol収率 53%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ce0b5e6577294b00b5a91d7826e477ad
出典データセット
uspto-grants-2007_10
特許番号
US07282512B2

反応ノート

読み込み中…