Water → HCID 67509523, compound

HRID 623490Notes

Reaction equation

HRID 623490 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:15](=[O:17])[CH3:16])[CH:6]=[N:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].[C:18](OC(=O)C)(=[O:20])[CH3:19].C(N(CC)CC)C.O>ClCCl>[C:18]([O:1][CH2:2][C:3]1[C:8]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])=[N:7][CH:6]=[C:5]([C:15](=[O:17])[CH3:16])[CH:4]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67508623HCID 67508623, compound

Product 1

HCID 67509523HCID 67509523, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(5-(hydroxymethyl)-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanone (0.16 g, 0.64 mmol, Step-6), acetic anhydride (0.18 mL, 1.91 mmol) and triethylamine (0.44 mL, 3.19) in dichloromethane (4 mL) is stirred at room temperature for 3 days. The reaction mixture is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo to give 0.16 g (86% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-8) without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-629f17c3e0614cc3ba8adab76dd50b2e
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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