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

HRID 1372909Notes

Reaction equation

HRID 1372909 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].[CH2:17]1[CH2:21]OC[CH2:18]1.[Cl-].[NH4+]>CCOC(C)=O>[NH2:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]([OH:15])([CH2:18][CH2:17][CH3:21])[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

90.0 mL (180.00 mmol) of propylmagnesium chloride (2 M in ether) are added dropwise within 30 min. to a solution of 7.00 mL (54.04 mmol) methyl anthranilate in abs. THF (70 mL) at 0° C. The mixture is stirred for 1 h at RT and then combined with 100 mL 3 M aqueous ammonium chloride solution and EtOAc. The phases are separated and the aqueous phase is exhaustively extracted with EtOAc. The combined org. phases are washed with aqueous KHCO3 and sat. aqueous NaCl and dried with sodium sulphate. The crude product is used in the next reaction step without any further purification.

Workup

  1. customat 0° C
  2. customThe phases are separated
  3. extractionthe aqueous phase is exhaustively extracted with EtOAc
  4. washphases are washed with aqueous KHCO3 and sat. aqueous NaCl
  5. dry with materialdried with sodium sulphate
  6. customThe crude product is used in the next reaction step without any further purification

Sources & evidence

ORD record
ord-745024b0c6214b8aac6d57ed4de4a9e8
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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