Triacetoxyperiodinane → Methyl 3-(2-cyclopropylacetyl)-4-methylbenzoate

HRID 1487830ノート

反応式

HRID 1487830 の反応式
[CH:1]1([CH2:4][CH:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[CH3:17])[C:10]([O:12][CH3:13])=[O:11])[OH:6])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:1]1([CH2:4][C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=2[CH3:17])[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 90033589Methyl 3-(2-cyclopropyl-1-hydroxyethyl)-4-methylbenzoate2 回

生成物 1

HCID 90021671Methyl 3-(2-cyclopropylacetyl)-4-methylbenzoate収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Into a 100-mL round-bottom flask, was placed a solution of methyl 3-(2-cyclopropyl-1-hydroxyethyl)-4-methylbenzoate (compound 4.4, 200 mg, 0.85 mmol) in dichloromethane (30 mL). This was followed by the addition of Dess-Martin periodinane (721 mg, 1.70 mmol) in portions at room temperature. The resulting solution was stirred for 1 h at room temperature, then quenched with saturated aqueous Na2S2O3 (30 mL). The resulting mixture was extracted with DCM (3×20 mL) and the combined organics was washed with brine (2×20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:5) as the eluent to yield the title compound as a yellow oil (150 mg, 75%).

後処理

  1. customInto a 100-mL round-bottom flask, was placed
  2. customquenched with saturated aqueous Na2S2O3 (30 mL)
  3. extractionThe resulting mixture was extracted with DCM (3×20 mL)
  4. washthe combined organics was washed with brine (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:5) as the eluent

出典と根拠

ORDレコード
ord-59521f3cdc5d4d9caae2a2630813c1e2
出典データセット
uspto-grants-2016_08
特許番号
US09428502B2

反応ノート

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