Benzoic Acid → HCID 178525789, compound
Reaction equation
[C:1]1([C@@H:7]2[CH2:10][C@H:9]([OH:11])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31](O)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(C(OCC)=O)=NC(OCC)=O>>[C:31]([O:11][C@H:9]1[CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:10]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1Participants
Procedure
To a stirred solution of cis-3-phenylcyclobutanol (Eckehard, V. D.; et al. Chem. Ber., 1993, 126, 2759., 4.6 g, 30.2 mmol), triphenylphosphine (3.3 g, 59.1 mmol) and benzoic acid (7.6 mg, 62.3 mmol) was added diethyl azodicarboxylate (DEAD) (10.9 g, 62.3 mmol) at room temperature. The resulting mixture was stirred at room temperature for 40 min, then the mixture was concentrated. The residue was dissolved in diethyl ether (100 mL) and washed with saturated aqueous sodium bicarbonate (50 mL), water (50 mL), and brine (50 mL). The organic layer was dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (10:1) to afford 6.52 g (86%) of the title compound as a pale yellow oil: 1H-NMR (CDCl3) δ 7.71–7.20 (10H, m), 5.49–5.41 (1H, m), 3.82–3.72 (1H, m), 2.78–2.64 (4H, m).
Workup
- concentrationthe mixture was concentrated
- dissolutionThe residue was dissolved in diethyl ether (100 mL)
- washwashed with saturated aqueous sodium bicarbonate (50 mL), water (50 mL), and brine (50 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated
- customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (10:1)
Sources & evidence
- ORD record
- ord-53e0c0d8072344f2891d5781f1e6f704
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148234B2
Reaction notes
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