2-Aminophenol → HCID 66726405, compound

HRID 2364944Notes

Reaction equation

HRID 2364944 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[O:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:9]1[CH2:14][CH2:13][CH:12]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66726405HCID 66726405, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-aminophenol (1 g, 9.164 mmol), tetrahydropyran-4-one (1.099 ml, 11.913 mmol), and sodium triacetoxy-borohydride (0.71 g, 3.42 mmol) in DCE (50 ml) was stirred at r.t. for 16 h. The crude was filtered over diatomaceous earth, washed with DCM and the filtrate was evaporated in vacuo to yield D7 (0.69 g) that was used as such in the next reaction step without further purification.

Workup

  1. filtrationThe crude was filtered over diatomaceous earth
  2. washwashed with DCM
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-741ccdfde3ef4498ac249d8e082daaf2
Source dataset
uspto-grants-2014_04
Patent number
US08697689B2

Reaction notes

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