Acetic Anhydride → 6-Nitro-isochroman-1,3-dione

HRID 580939노트

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HRID 580939 반응식
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[N+:14]([C:12]1[CH:13]=[C:5]2[C:6](=[CH:10][CH:11]=1)[C:7](=[O:9])[O:8][C:1](=[O:2])[CH2:4]2)([O-:16])=[O:15]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 71720252-(Carboxymethyl)-4-nitrobenzoic acid

생성물 1

HCID 156814366-Nitro-isochroman-1,3-dione수율 88%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2 carboxymethyl-4-nitro-benzoic acid (13 g, 57.7 mmol), acetic anhydride (5.45 mL, 57.7 mmol) and toluene (30 mL) were heated to reflux for 5 hrs. The solvent was removed under vacuum to yield 6-nitro-isochroman-1,3-dione (compound (3a) in Scheme 2) as a yellow solid (10.51 g, 88%). Borane tetrahydrofuran complex (35.6 mL, 1M in THF) was added dropwise over 40 min to a solution of 6nitro-isochroman-1,3-dione (2 g, 9.66 mmol) in THF (40 mL) at 0° C. The contents were stirred for 18 hrs at 25° C., cooled to 0° C., quenched with methanol (30 mL), and stirred for 1 hr. The solvents were removed under vacuum, ethyl acetate (30 mL) added and the organic phase washed with 10% aqueous hydrochloric acid. The aqueous acidic layer was reextracted with ethyl acetate (30 mL), the combined organic layers dried with magnesium sulfate, and evaporated under vacuum until 2 mL of ethyl acetate remained. This solution was filtered through silica gel washing with methylene chloride (30 mL) to remove impurities. The silica gel was flushed with ethyl acetate, solvent removed under vacuum to give a solid which was slurryed in methylene chloride and filtered to afford the diol as a white solid, 1.38 g, 73%.

후처리

  1. temperaturewere heated
  2. temperatureto reflux for 5 hrs
  3. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-8725c0e159ee4e188b7729c59d9f8c8d
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919795

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