Tetrahydrofuran → 4-(2-Aminophenyl)heptan-4-ol

HRID 2223120Notes

Reaction equation

HRID 2223120 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].[C:6]([O:15]C)(=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH2:9].[Cl-].[NH4+].CCOC(C)=O.[CH2:25]1[CH2:29]OC[CH2:26]1>>[NH2:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]([OH:15])([CH2:26][CH2:25][CH3:29])[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8635Methyl AnthranilateHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 178455855HCID 178455855, compound

Product 1

HCID 210728384-(2-Aminophenyl)heptan-4-ol

Procedure

90.0 mL (180.00 mmol) of propylmagnesium chloride (2 M in ether) is added dropwise within 30 minutes to a solution of 7.00 mL (54.04 mmol) methyl anthranilate in absolute THF (70 mL) at 0° C. The mixture is stirred for 1 hour at RT and then combined with 100 mL of 3 M aqueous ammonium chloride solution and EtOAc. The phases are separated and the aqueous phase is exhaustively extracted with EtOAc. The combined organic phases are washed with aqueous KHCO3 and saturated aqueous NaCl and dried with sodium sulfate. The crude product is used in the next reaction step without any further purification. Yield: 6.70 g (60%).

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is exhaustively extracted with EtOAc
  3. washThe combined organic phases are washed with aqueous KHCO3 and saturated aqueous NaCl
  4. dry with materialdried with sodium sulfate
  5. customThe crude product is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-bf921ee917b84b0a8d65ec369d0abd16
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

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