Sodium Thiosulfate → HCID 12166520, compound

To a solution of (E)-3-cyclohexylpent-2-enol (1.50 g, 8.91 mmol) in dichloromethane (45 mL), cooled to 0° C., was added Dess-Martin periodinane (9.7 g, 22.9 mmol). The resulting suspension was warmed to room temperature and stirred for approximately 2 h until the reaction was judged to be complete by TLC. The reaction was poured into 100 mL of saturated aqueous NaHCO3 containing Na2S2O3 (3 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 (5% Et2O/pentane) to afford the title compound (1 g, 68% yield) as a colorless oil that was a 3:1 mixture of E:Z isomers. Major isomer: IR (film) 2927, 2746, 1668, 1622, 1450, 1189, 1124, 860 cm−1; 1H NMR (300 MHz, CDCl3) δ 10.04 (d, 1H, J=8.24 Hz, CHO), 5.83 (d, 1H, J=8.24 Hz, C═CH), 2.61 (q, 2H, J=7.4 Hz, CH2CH3), 2.07 (tt, 1H, J=2.6, 11.0 Hz, CH2CHCH2), 1.88-1.71 (m, 5H), 1.41-1.15 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 191.8, 175.2, 124.9, 46.2, 31.9, 26.5, 26.3, 26.0, 25.9, 24.2, 15.4; HRMS (EI+) exact mass calculated for [M]+ (C11H18O) requires m/z 166.1358, found m/z 166.1355.

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 (5% Et2O/pentane)

ORD record

ord-80a2c7c868964b6aac893726cedbc648

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323604B2