Triacetoxyperiodinane → 3-(Benzyloxy)-2-methylbenzaldehyde

HRID 253398ノート

反応式

HRID 253398 の反応式
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH2:15][OH:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[C:11]([CH:12]=[CH:13][CH:14]=1)[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 58087471(3-Benzyloxy-2-methyl-phenyl)-methanol

生成物 1

HCID 159481993-(Benzyloxy)-2-methylbenzaldehyde収率 88.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (3-benzyloxy-2-methyl-phenyl)-methanol (57, 627 mg, 2.75 mmol) in tetrahydrofuran (60 mL) was added Dess-Martin periodinane (2.9 g, 6.87 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 50 minutes. The reaction mixture was quenched with a solution of saturated sodium thiosulfate, extracted with ethyl acetate, washed with sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a white solid (58, 0.55 g, 84%).

後処理

  1. customThe reaction mixture was quenched with a solution of saturated sodium thiosulfate
  2. extractionextracted with ethyl acetate
  3. washwashed with sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane

出典と根拠

ORDレコード
ord-c631cea09bc344879b4b90d66efc94f8
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

反応ノート

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