Acetic Acid → 1-(2-Nitro-ethyl)-4-phenoxymethyl-benzene

HRID 78052ノート

反応式

HRID 78052 の反応式
C(O)(=O)C.[N+:5](/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6].[BH4-].[Na+]>CS(C)=O>[N+:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592552121-((E)-2-Nitro-vinyl)-4-phenoxymethyl-benzene

生成物 1

HCID 592554571-(2-Nitro-ethyl)-4-phenoxymethyl-benzene収率 51%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To an acetic acid (4.1 mL) and dimethyl sulfoxide (70 mL) solution of 1-((E)-2-nitro-vinyl)-4-phenoxymethyl-benzene (4.1 g, 16.2 mmol) described in Manufacturing Example 86-1-3 was added sodium borohydride (981 mg, 25.9 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1 hour at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (2.11 g, 51%).

後処理

  1. temperaturewhile cooling appropriately
  2. customThe mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-1406e6ac21514bc4a56da379e84dd83a
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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