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

HRID 1028874Notes

Reaction equation

HRID 1028874 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]+

Workup

  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

Sources & evidence

ORD record
ord-f3b36e9fa0b341099247f4ef291242e7
Source dataset
uspto-grants-2014_05
Patent number
US08735627B2

Reaction notes

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