Pyridine → 3-Nitro-1-(4-octylphenyl)propyl acetate

HRID 1028874ノート

反応式

HRID 1028874 の反応式
[N+:1]([CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=1)=[O:7])([O-:3])=[O:2].[BH4-].[Na+].N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>CO.C(OCC)(=O)C.ClCCl>[C:30]([O:7][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:13]=1)[CH2:5][CH2:4][N+:1]([O-:3])=[O:2])(=[O:32])[CH3:31]

参加物

8

反応物 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 715785353-Nitro-1-(4-octylphenyl)propan-1-one

生成物 1

HCID 569680573-Nitro-1-(4-octylphenyl)propyl acetate収率 94%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-nitro-1-(4-octylphenyl)propan-1-one (12) (5.00 g) in methanol (25 ml) was added sodium borohydride (0.8 g) at 0° C. and the mixture was left at room temperature for 4.5 hr. The suspension was diluted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous Na2SO4 and concentrated. To the residue was added pyridine (1.5 eq), dichloromethane (10 v) and acetic anhydride (10 eq), and the mixture was left at room temperature overnight. To the reaction mixture was added ice water and the mixture was extracted with ethyl acetate and washed successively with 1 N HCl, sodium bicarbonate solution and brine. The ethyl acetate solution was dried over sodium sulfate and concentrated. The residue was pure enough for transformation to the next step or can be purified by silica gel column chromatography using hexane-ethyl acetate as eluent. Yield=94%, ESIMS 358.2 [M+Na]+

後処理

  1. washwashed successively with 1 N HCl, sodium bicarbonate solution and brine
  2. dry with materialThe ethyl acetate layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. waitthe mixture was left at room temperature overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washwashed successively with 1 N HCl, sodium bicarbonate solution and brine
  7. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  8. concentrationconcentrated
  9. customcan be purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-f3b36e9fa0b341099247f4ef291242e7
出典データセット
uspto-grants-2014_05
特許番号
US08735627B2

反応ノート

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