Diethyl Ether → HCID 69222271, compound

HRID 2253433Notes

Reaction equation

[CH:1]1([CH:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC[O:16]CC>>[CH:1]1([C@@H:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:16])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 3283Diethyl Ether

HCID 69221752HCID 69221752, compound

Product 1

HCID 69222271HCID 69222271, compoundYield 80%

Procedure

Prepared according to the general procedure from 3-cyclohexylcyclohexen-2-one (178 mg, 1.09 mmol) in 0.2 M Et2O for 43 h at room temperature to provide the title compound as a colorless oil (157 mg, 80% yield, 90% ee) after purification by flash chromatography on silica gel (5% Et2O/pentane). The enantiomeric ratio was determined by GLC using a Hydrodex-B-TBDAc (50 m×0.25 mm) column (110° C. isotherm, 1 mL/min.); (S) isomer tr=73.5 min. and (R) isomer tr=65.2 min. IR (film) 2924, 2853, 1715, 1449, 14223, 1346, 1317, 1263, 1225, 1101, 1056, 982, 892, 866 cm−1; 1H NMR (300 MHz, CDCl3) δ 2.44-2.21 (m, 3H), 2.16-2.04 (m, 2H), 1.93-1.85 (m, 1H), 1.80-1.54 ((m, 8H), 1.47-1.33 (m, 1H), 1.32-1.11 (m, 3H), 1.08-0.92 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 212.9, 45.6, 44.7, 42.7, 41.6, 30.0, 29.9, 28.4, 26.6, 26.59, 25.54, 25.6; HRMS (EI+) exact mass calculated for [M]+ (C12H20O) requires m/z 180.1514, found m/z 180.1508; [α]D22+11.9° (c=1.05, CHCl3).

Workup

customPrepared

Sources & evidence

ORD record: ord-43f74b68ed404ff68385192fed722b76
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323604B2

Reaction notes

Loading…