Acetic Anhydride → HCID 178471965、化合物

HRID 1859488

反応式

HRID 1859488 の反応式
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[CH3:19]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(OC(OCC)OCC)C.C(OC(=O)C)(=O)C.Cl.[NH2:61][C:62]1[C:71]2[C:66](=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:65]=[CH:64][C:63]=1[OH:72]>ClCCl.N1C=CC=CC=1>[OH:72][C:63]1[CH:64]=[CH:65][C:66]2[C:71](=[CH:70][CH:69]=[CH:68][CH:67]=2)[C:62]=1[NH:61][CH:19]=[C:6]([C:4]([C:3]1[CH:12]=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:2]=1[F:1])=[O:5])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

8

反応物 5

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 5184691-Amino-2-naphthol hydrochlorideHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate2 回HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

生成物 1

HCID 178471965HCID 178471965、化合物収率 93%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒2 回HCID 6344Dichloromethane溶媒2 回

反応条件

温度
130 °C

実験手順

Ethyl 2,3,4,5-tetrafluorobenzoylacetate was treated with triethyl orthofomate and acetic anhydrate, then with different aminonaphthols in the presence of pyridine to generate an aminoketoacid. The solution of ethyl 2,3,4,5-tetrafluorobenzoylacetate (1.10 g, 4.18 mmol) in triethylorthoformate (1 ml, 6.06 mmol) and acetic anhydride (1.8 ml, 19 mmol) was heated and stirred at 130° C. for 4 h. During the process, the formed ethyl acetate was removed. The mixture was then distilled under vacuum to yield an orange oil, which was dissolved in 30 ml dichloromethane. 1-aminonaphthalen-2-ol hydrogen chloride (90% pure from Aldrich) (1.36 g, 6.26 mmol), premixed with 2 equivalent of pyridine, was added to the dichloromethane solution, and the mixture was stirred overnight at 22° C. After the solvent was removed under reduced pressure, the remaining residue was absorbed on silica gel and subjected to flash column chromatography (gradient ethylacetate:hexanes=8:4) that yield a bright yellow powder (1.69 g). Yield=93%. 1H NMR (CDCl3) δ 1.02 (t, J=7.2 Hz, 3H), 4.01 (q, J=7.2 Hz, 2H), 4.10 (m, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.41 (m, 1H), 7.60 (m, 2H), 7.82 (8, 2H), 7.91 (d, J=8.1 Hz, 1H), 8.54 (b, 1H).

後処理

  1. customDuring the process, the formed ethyl acetate was removed
  2. distillationThe mixture was then distilled under vacuum
  3. customto yield an orange oil, which
  4. stirringthe mixture was stirred overnight at 22° C
  5. customAfter the solvent was removed under reduced pressure
  6. customthe remaining residue was absorbed on silica gel

出典と根拠

ORDレコード
ord-90f4cdb0eb8140d2bacc64d5a78b5d63
出典データセット
uspto-grants-2003_03
特許番号
US06528517B1

関連ノート

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