Tropic acid → 3-phenyloxetan-2-one

HRID 898682

Reaction equation

CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([OH:43])(=[O:42])[CH:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:34]O>O1CCCC1>[C:36]1([CH:33]2[CH2:34][O:43][C:32]2=[O:42])[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

Conditions

Temperature: -10 °C

Procedure

Diethylazodicarboxylate (DEAD) (1.89 milliliter (mL), 12.0 millimole (mmol)) was added dropwise to a stirred solution of triphenylphosphine (3.18 gram (g), 12.0 mmol) in dry tetrahydrofuran (THF) (40 mL) at −78° C. under nitrogen (N2). Tropic acid (2.00 g, 12.0 mmol) in dry THF (40 mL) was then added dropwise, and the resulting mixture was stirred and slowly warmed to −10° C., at which point the solution was homogeneous. After concentration and purification by flash chromatography on silica gel (petroleum ether/ethyl acetate (EtOAc) 85:15), 3-phenyloxetan-2-one (1.49 g, 84%) (see Mulzer, J.; Kerkmann, T. J. Am. Chem. Soc. 1980, 102, 3620-3622) was isolated as a yellow oil: 1H NMR (270 MHz, CDCl3) δ 7.3 (m, 5H), 4.8 (dd, J=5.0, 1.7 Hz, 1H), 4.5 (dd, J=5.0, 1.7 Hz, 1H), 4.2 (dd, J=5.0, 5.0 Hz, 1H).

Workup

concentrationAfter concentration and purification by flash chromatography on silica gel (petroleum ether/ethyl acetate (EtOAc) 85:15)

Sources & evidence

ORD record: ord-10719aacf42d494eac8faaefea34d6a8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351827B2

Linked notes

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