Hydrogen Peroxide → Benzyl 5-hydroxy-2,2-dimethylpentanoate

HRID 1864816ノート

反応式

HRID 1864816 の反応式
[CH3:1][C:2]([CH3:16])([CH2:13][CH:14]=[CH2:15])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].B1C2CCCC1CCC2.C([O-])(=[O:28])C.[Na+].OO>C1COCC1>[OH:28][CH2:15][CH2:14][CH2:13][C:2]([CH3:16])([CH3:1])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 517045Sodium AcetateHCID 66973286Benzyl 2,2-dimethylpent-4-enoate

生成物 1

HCID 66972971Benzyl 5-hydroxy-2,2-dimethylpentanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of benzyl 2,2-dimethylpent-4-enoate (5.74 g, 26.3 mmol, prepared according to Step A) in THF (100 mL) was added a solution of 9-BBN (63.1 mL, 31.6 mmol, 0.5 M in THF) over 20 minutes, while under nitrogen. The reaction was allowed to stir at ambient temperature for 17 hours. An aqueous solution of sodium acetate (7.3 g, 89 mmol, in 18 mL of water) was then added, followed by the slow addition of aqueous hydrogen peroxide (18 mL, 30% by weight solution) with occasional chilling in a 0° C. bath. This mixture was allowed to stir at ambient temperature for 1.5 hours, before being extracted with ethyl acetate. The combined organics were washed with saturated brine. The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM-1:99 to 10:90, to give the title compound. MS: m/z=237 (M+1).

後処理

  1. temperaturewith occasional chilling in a 0° C. bath
  2. stirringto stir at ambient temperature for 1.5 hours
  3. extractionbefore being extracted with ethyl acetate
  4. washThe combined organics were washed with saturated brine
  5. dry with materialThe organics were then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue that
  9. customwas purified by silica gel chromatography
  10. washeluting with a gradient of MeOH

出典と根拠

ORDレコード
ord-0e41c0dd9e624322af6fc903a2f306a8
出典データセット
uspto-grants-2009_12
特許番号
US07625901B2

反応ノート

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