Water → HCID 131718559, compound

HRID 1728995Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]([CH2:11][CH2:12][C@H:13]1[CH2:18][C@H:17]2[CH2:19][C@H:15]([C:16]2([CH3:21])[CH3:20])[C@@H:14]1[CH3:22])[CH:9]=[O:10].O.[OH-].[Na+]>C(OCC)C>[CH3:7][CH:8]([CH2:11][CH2:12][C@H:13]1[CH2:18][C@H:17]2[CH2:19][C@H:15]([C:16]2([CH3:20])[CH3:21])[C@@H:14]1[CH3:22])[CH2:9][OH:10]

Participants

Conditions

Temperature: 10 °C

Procedure

7.9 ml (7.9 mmol) of 1M LiAlH4 solution in ethyl ether and 6 ml of anhydrous ethyl ether are charged under nitrogen into a 25 ml three-necked flask equipped with a thermometer, a condenser and a magnetic stirrer and 3.5 g (15.7 mmol) of (R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]butanal diluted in 6 ml of the same solvent are then added. The mixture is heated at reflux for 2 h. and is then cooled to 10° C. 0.3 ml of water, 0.3 ml of 15% aqueous NaOH solution and 0.8 ml of water are added successively and stirring is maintained for 10 minutes. After filteration through kieselguhr and evaporation of the ether phase the residue is purified by flash chromatography on silica (eluent: petroleum ether/ethyl ether 93:7) and distilled in a bulb-tube (Kugelrohr) to give 2.85 g of (R/S)-2-methyl-4-[(1S,2R,3S,5S)-3-pinanyl]-1-butanol (yield 81%).

Workup

additionare then added
temperatureThe mixture is heated
temperatureat reflux for 2 h.
temperatureis maintained for 10 minutes
customAfter filteration through kieselguhr and evaporation of the ether phase the residue
customis purified by flash chromatography on silica (eluent: petroleum ether/ethyl ether 93:7)
distillationdistilled in a bulb-tube (Kugelrohr)

Sources & evidence

ORD record: ord-732bcd24157d41418c17d6b080fa8cc0
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05329052

Reaction notes

Loading…