反应详情

温度

-78 °C

(II, where R1, R2, R3 and R4 are methyl) To 40 mg (0.16 mmol) of methyl (2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate I in 2 mL of anhydrous tetrahydrofuran (THF) at -78° C. was added (0.25 mmol) of LiAlH4. The reaction was stirred at -78° C. for 15 min and warmed to room temperature (RT). When the reaction was complete, as monitored by thin-layer chromatography (TLC), 2 mL of H2O was added and the organics extracted with ether and washed 3 X with 5 mL of water. The organic layer was dried with MgSO4, filtered, concentrated in vacuo and the dienol II was used directly in the next step. TLC (20% EtOAc-hexane) Rf 0.26 (cis isomer), 1H-NMR δ1.01 (s, (CH3)2), 1.46 (t, J=6 Hz, CH2 ), 1.62 (dr, J= 6 Hz, J=4 Hz, CH2), 1.70 (s, CH3, 1.91 (s, CH3), 2.01 (t, J=6 Hz, CH2), 4.30 (d, J=6 Hz, CH2 ), 5.54(t,J=6 Hz, CH), 6.19 (d, J=16 Hz, CH), 6.39 (d, J=16 Hz, CH).

1. temperaturewarmed to room temperature (RT)
2. additionwas added
3. extractionthe organics extracted with ether
4. washwashed 3 X with 5 mL of water
5. dry with materialThe organic layer was dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo