Acetone → Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate

HRID 1845309ノート

反応式

HRID 1845309 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=C(C=C)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[N+]1([O-])CC[O:18]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+].[CH3:29][C:30]([CH3:32])=[O:31]>O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:29]([CH:30]([OH:31])[CH2:32][OH:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

7

反応物 4

HCID 180AcetoneHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 58188041Methyl 3-bromo-5-vinylbenzoate

生成物 1

HCID 58188335Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回

実験手順

To a stirred solution of methyl 3-bromo-5-vinylbenzoate (1.6 g, 6.6 mmol) and N-methylmorpholine N-oxide (2.0 g, 17.1 mmol) in acetone (40 mL) and water (10 mL) was added dropwise a 5% solution of osmium tetraoxide in water (0.50 g, 0.10 mmol). The reaction mixture was stirred at rt for 3 h, and then a saturated aq. Na2S2O3 solution was added. After being stirred for 30 min, the reaction mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.

後処理

  1. stirringAfter being stirred for 30 min
  2. extractionthe reaction mixture was extracted with EtOAc (100 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

出典と根拠

ORDレコード
ord-fae21d0f18f648d9a4efd15ec940dc02
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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