Trifluoroacetic acid → 2-[4-(Methoxycarbonyl)oxan-4-yl]acetic acid

HRID 30848

Reaction equation

HRID 30848 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][C:8]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:17][O:16][C:14]([C:8]1([CH2:7][C:6]([OH:18])=[O:5])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21985691methyl 4-(2-tert-butoxy-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 219856952-[4-(Methoxycarbonyl)oxan-4-yl]acetic acidYield 104.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(2-tert-butoxy-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate (1.1 g, 4.26 mmol) in dichloromethane (5.0 mL) was added trifluoroacetic acid (5.0 mL) and the resulting solution was stirred at rt for 5 h. The mixture was concentrated under reduced pressure to afford [4-(methoxycarbonyl)tetrahydro-2H-pyran-4-yl]acetic acid (900 mg, 94%), which was used in the next step without further purification. LC-MS ret. time 0.93 min, m/z 202.9 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 1.60-1.70 (m, 2H), 2.10-2.15 (m, 2H), 2.68 (s, 2H), 3.62-3.71 (m, 2H), 3.72 (s, 3H), 3.79-3.86 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b87bd52bebc4f5e84cdd400e0f932e8
Source dataset
uspto-grants-2008_09
Patent number
US07423156B2

Linked notes

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