2-Aminophenol → HCID 66726640, compound

HRID 2361746Notes

Reaction equation

HRID 2361746 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[O:9]1[C:13]2([CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C(Cl)Cl>[O:9]1[C:13]2([CH2:18][CH2:17][CH:16]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[OH:8])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1

Participants

7

Reactant 3

HCID 58012-AminophenolHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66726640HCID 66726640, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-aminophenol (2 g, 18.327 mmol), 1,4-dioxa-spiro[4.5]decan-8-one (3.721 g, 23.825 mmol), and sodium triacetoxyborohydride (5.826 g, 27.491 mmol) in DCE (20 ml) and acetic acid (0.2 ml) was stirred at room temperature for 3 h. The reaction mixture was diluted with DCM and washed with NaHCO3 (aqueous sat. solution), dried (Na2SO4) and the solvent was evaporated in vacuo. The solid residue was triturated with diisopropyl ether to yield D19 (3.78 g) as a white solid.

Workup

  1. washwashed with NaHCO3 (aqueous sat. solution)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe solid residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-48e4d513f8ae413081d3fd7ffcf4a201
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

Loading…