Acetic Acid → 1-Benzyloxy-3-(2-nitro-ethyl)-benzene

HRID 1891669

반응식

HRID 1891669 반응식
C(O)(=O)C.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](/[CH:19]=[CH:20]/[N+:21]([O-:23])=[O:22])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>CS(C)=O>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][N+:21]([O-:23])=[O:22])[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 53682823-Benzyloxy-trans-beta-nitrostyrene

생성물 1

HCID 592552051-Benzyloxy-3-(2-nitro-ethyl)-benzene수율 57%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To an acetic acid (5.5 mL) and dimethyl sulfoxide (94 mL) solution of 1-benzyloxy-3-((E)-2-nitro-vinyl)-benzene (5.5 g, 21.5 mmol) described in Manufacturing Example 61-1-2 was added sodium borohydride (1.3 g, 34.4 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1.5 hours at room temperature. This 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=10:1-4:1) to obtain the title compound (3.14 g, 57%).

후처리

  1. temperaturewhile cooling appropriately
  2. customThis 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=10:1-4:1)

출처 및 근거

ORD 기록
ord-26677696cdb2473abb84f7a5277dbfdc
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507530B2

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