Ethanol → 6-(Ethoxycarbonyl)chromane-2-carboxylic acid

HRID 1007765Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6][CH2:5]2.C(N(CC)CC)C.C(O)C.[C:25]([O:28][CH2:29][CH3:30])(=[O:27])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:28][C:25]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]([OH:14])=[O:13])[CH2:6][CH2:5]2)=[O:27])[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

A 2-neck round bottom flask fit with a reflux condenser was charged the compound from Example 28 (1.05 g, 3.45 mmol) and palladium (II) acetate (23 mg, 0.10 mmol). The flask was placed under an atmosphere of carbon monoxide (1 atm). Triethylamine (1.20 mL, 8.63 mmol) and absolute ethanol (2.0 mL) were added via syringe. The dark reaction mixture was heated to 60° C. and stirred for 60 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The resulting dark solution was washed sequentially with 7% aqueous hydrochloric acid, water, and saturated aquesous sodium chloride. The organic layer was dried (MgSO4), and concentrated to an orange oil which crystallized on standing to a pale solid (0.675 g, 81%). 1H NMR (300 MHz, DMSO-d6) δ 13.03 (s, 1H), 7.68 (m, 2H), 6.90 (m, 1H), 4.89 (m, 1H), 4.25 (q, J=7.36 Hz, 2H), 2.82 (m, 1H), 2.66 (m, 1H), 1.28 (t, J=6.98 Hz, 3H); MS (CI) m/z 251 (MH+).

Workup

customThe dark reaction mixture
temperatureThe reaction mixture was cooled to room temperature
washThe resulting dark solution was washed sequentially with 7% aqueous hydrochloric acid, water, and saturated aquesous sodium chloride
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated to an orange oil which
customcrystallized

Sources & evidence

ORD record: ord-988f24ceedfd4b6e9c1834ba37b72532
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797714B2

Reaction notes

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