Sodium Thiosulfate → HCID 12166684, compound

Temperature

23 °C

To a solution of (E)-3-cyclohexylbut-2-enol (700 mg, 4.54 mmol) in dichloromethane (11 mL), cooled to 0° C., was added Dess-Martin periodinane (2.11 g, 4.99 mmol). The resulting suspension was warmed to 23° C. and stirred for approximately 30 minutes until the reaction was judged to be complete by TLC. The reaction mixture was poured into 50 mL of saturated aqueous NaHCO3 containing Na2S2O3 (1 g). This mixture was stirred vigorously until both layers became clear. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (25% EtOAc/hexanes) to afford the title compound as a colorless oil (350 mg, 51% yield) that was a 5.2:1 mixture of E:Z isomers. Major isomer: IR (film) 2929, 2854, 1729, 1674, 1640, 1450, 1383, 1198, 1164, 894, 850, 522 cm−1; 1H NMR (300 MHz, CDCl3) δ 10.05 (d, 1H, J=7.9 Hz CHO), 5.90 (dq, 1H, J=1.1, 7.9 Hz, C═CH), 2.18 (d, 3H, J=1.3 Hz, CH3), 2.09-2.02 (m, 1H, CH2CHCH2), 1.87-1.70 (m, 5H), 1.40 (m, 5H); 13C NMR (75 MHz, CDCl3) δ 191.9, 168.8, 125.8, 48.4, 31.4, 31.2, 26.3, 26.1, 26.0, 16.1; HRMS (EI+) exact mass calculated for [M]+ (C10H16O) requires m/z 152.1201, found m/z 152.1205.

1. stirringThis mixture was stirred vigorously until both layers
2. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
3. dry with materialthe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by flash chromatography (25% EtOAc/hexanes)

ORD record

ord-a725a8847b034529ba84d448a591fa0b

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323604B2