Hydrochloric Acid → HCID 58557499, compound

HRID 1969545Notes

Reaction equation

HRID 1969545 reaction equation
Cl.[CH2:2]([CH:4]1[CH2:8][CH:7]([CH2:9][OH:10])[CH2:6][CH:5]1[C:11]([OH:13])=[O:12])[CH3:3].[CH3:14][CH2:15]O>>[CH2:2]([CH:4]1[CH2:8][CH:7]([CH2:9][OH:10])[CH2:6][CH:5]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 58557434HCID 58557434, compound

Product 1

HCID 58557499HCID 58557499, compoundYield 58%

Conditions

Temperature
25 °C

Procedure

HCl gas was bubbled through a solution of 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylic acid (7.29 g, 42.3 mmol) in EtOH (60 mL) at about 25° C. for about 10 min. The reaction mixture was stirred at about 25° C. for about 72 h. The solvent was removed under reduced pressure. The crude residue was partitioned between water (30 mL) and DCM (3×30 mL). The combined organic extracts were concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc/heptane to give ethyl 2-ethyl-4-(hydroxymethyl)cyclopentanecarboxylate (4.89 g, 58%) as a yellow oil: 1H NMR (CDCl3) δ 4.23-4.02 (m, 2H), 3.74-3.47 (m, 2H), 2.96-2.83 (m, 1H), 2.31-2.17 (m, 1H), 2.15-1.98 (m, 2H), 1.97-1.84 (m, 1H), 1.79-1.66 (m, 1H), 1.65-1.50 (m, 1H), 1.49-1.37 (m, 1H), 1.30-1.21 (m, 5H), 1.04-0.82 (m, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude residue was partitioned between water (30 mL) and DCM (3×30 mL)
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with a gradient of 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-6b3487b13380455d88f6373158f69aba
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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