Formic Acid → HCID 22145868, compound

HRID 1092844Notes

Reaction equation

HRID 1092844 reaction equation
[CH:1]([OH:3])=O.[CH:4]1([O:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]=[C:12](OC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1>C(OCC)(=O)C>[CH:4]1([O:9][C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]=[C:12]([CH2:1][OH:3])[CH:11]=2)[CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 22145749HCID 22145749, compound

Product 1

HCID 22145868HCID 22145868, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

90% Formic acid (5.5 mL) is added to a suspension of 4-cyclopentyloxy-5-methoxy-2-trityloxypyridine (1.2 g) in ethyl acetate (8.5 mL) and the mixture stirred at room temperature for 1 hours. The mixture is diluted with ethyl acetate and washed with brine then aqueous sodium bicarbonate until the washings are neutral. The brine washings are neutralised with solid sodium bicarbonate and extracted with ethyl acetate. After drying (MgSO4) the extracts are evaporated to give 4-cyclopentyloxy-2-hydroxymethyl-5-methoxypyridine (360 mg) as a white solid, m.p. 93-94.5° C. [Elemental analysis: C, 64.7; H, 7.80; N, 6.11%. calculated: C, 64.55; H, 7.68; N, 6.27%.].

Workup

  1. washwashed with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter drying (MgSO4) the extracts
  4. customare evaporated

Sources & evidence

ORD record
ord-5c6db666145d43b198afc604cb51a7e2
Source dataset
uspto-grants-2012_03
Patent number
US08129537B2

Reaction notes

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