Hydrochloric Acid → 2-Hydroxymethylene-5-methoxy-1-indanone

HRID 585903Notes

Reaction equation

C[O-].[Na+].[CH:4](OCC)=[O:5].[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[C:16](=[O:20])[CH2:15][CH2:14]2.Cl>C1COCC1>[OH:5][CH:4]=[C:15]1[CH2:14][C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH3:9])[CH:12]=2)[C:16]1=[O:20]

Participants

Conditions

Temperature: 23 °C

Procedure

To a mixture of sodium methoxide (1.2 g, 22 mmol) in THF (20 mL) was added ethyl formate (1.6 g, 22 mmol) and 5-methoxy-1-indanone (3.24 g, 19.7 mmol) and the mixture stirred for 16 h at 23° C. The reaction mixture was added to aqueous HCl (0.1 N) and extracted with a mixture (1:1) of ethyl acetate and ether (2×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated to a residue, which was purified by chromatography (silica, 40% ethyl acetate in hexanes) to give an oil (2.6 g, 69%): 1H NMR (CDCl3) δ 7.81 (d, J=9.6 Hz, 1H), 7.47 (s, 1H), 7.00 (m, 2H), 3.94 (s, 3H), 3.9 (m, 2H); MS m/z 191 [M+H]+.

Workup

extractionextracted with a mixture (1:1) of ethyl acetate and ether (2×20 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated to a residue, which
customwas purified by chromatography (silica, 40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-0fae55d1e66346958c2d7e83321d555c
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06933392B2

Reaction notes

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