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3-Nitrobenzaldehyde → [Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl ester

HRID 45810
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HRID 45810 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:19][O:20][P:21]([O-:24])[O:22][CH3:23]>C(OCC)(=O)C>[CH3:19][O:20][P:21]([CH:7]([OH:8])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:24])[O:22][CH3:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 74493-NitrobenzaldehydeHCID 8471TriethylamineHCID 21884954Dimethylphosphite

생성물 1

HCID 11299958[Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl ester수율 77%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

3-Nitrobenzaldehyde (20 g, 0.132 mol) was dissolved in 100 mL of ethyl acetate. Triethylamine (22 mL, 0.158 mol, 1.2 eq) was added, followed by dimethylphosphite (15.7 mL, 0.171 mmol, 1.3 eq) and the mixture was stirred at room temperature. After 2 hours the mixture was diluted with 150 mL of ethyl acetate and washed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was treated with ethyl ether to obtain a beige solid, which was filtered and dried under vacuum at 40° C. for 1 h (26.7 g, 77% yield).

후처리

  1. washwashed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with ethyl ether
  5. customto obtain a beige solid, which
  6. filtrationwas filtered
  7. customdried under vacuum at 40° C. for 1 h (26.7 g, 77% yield)

출처 및 근거

ORD 기록
ord-6b6d0775abb64f6ba1883c5aa00c22cb
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541575B2

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