thf thf 409 g was placed in a glass low pressure reactor and cooled to approximately u2212 20 u00b0 c n buli 60 ml of 10m was placed in a fisher porter bottle and chilled to approximately 0 u00b0 c n buli was added to the thf over about 15 minutes the solvation reaction was exothermic causing the mixture to rise in temperature up to approximately u2212 9 u00b0 c midway through the thf addition hydrogen was introduced to the vessel at approximately 35 psig the reactor was kept at u2212 15 to u2212 20 u00b0 c during the hydrogenation period of 8 hours an ir spectrum of a filtered sample of the slurry showed a small peak at 1612 cm u2212 1 for the lithium enolate of acetaldehyde calculated amount of deprotonation was 0 7 mol the lih slurry was quenched with methanol and discarded thf was added to the n buli n buli 250 ml of 2 5m was placed in a glass low pressure reactor and cooled to approximately u2212 20 u00b0 c hydrogen was introduced to the vessel at approximately 35 psig thf 493 g was placed in a fisher porter bottle and chilled to approximately u2212 20 u00b0 c thf was added slowly to the n buli to control the exotherm the temperature during the thf addition was kept below approximately 0 u00b0 c the reactor was kept at approximately u2212 10 to.