Methanol → HCID 11423659, compound

To a solution of 5 g of ethyl (R)-2,2,4-trimethyl-1,3-dioxolan-4-carboxylate in 30 ml of anhydrous ether, cooled down to -78°, were added dropwise while stirring for about 30 minutes, 4.55 g of diisobutylaluminium hydride in 25 ml of anhydrous ether. The temperature was held at -78° during the entire addition. The stirring was continued at -70° for a further 5 hours in order to complete the reaction. Excess reagent was then decomposed by cautious addition of a mixture of 2 ml of methanol and 2 ml of water, the cooling bath was removed and the reaction mixture was slowly brought to room temperature. While vigorously stirring under ice-cooling, 5 ml of 1-M sodium bicarbonate were added thereto. The addition of a total of 3 g of solid sodium bicarbonate in small portions led to the precipitation of aluminium hydroxide. After further vigorous stirring at 0° for 30 minutes, the precipitate was filtered off and washed three times with 30 ml of ether. The combined ether phases were dried over magnesium sulfate and the solvent was distilled off under normal pressure at about 65° bath temperature. The residue was distilled at about 80° bath temperature and 12 mmHg and there were thus obtained 3.2 g of (R)-4-formyl-2,2,4-trimethyl-1,3-dioxolan.

1. additionwere added dropwise
2. additionThe temperature was held at -78° during the entire addition
3. waitThe stirring was continued at -70° for a further 5 hours in order
4. customthe reaction
5. customthe cooling bath was removed
6. customwas slowly brought to room temperature
7. stirringWhile vigorously stirring under ice-
8. temperaturecooling
9. addition5 ml of 1-M sodium bicarbonate were added
10. additionThe addition of a total of 3 g of solid sodium bicarbonate in small portions
11. customled to the precipitation of aluminium hydroxide
12. stirringAfter further vigorous stirring at 0° for 30 minutes
13. filtrationthe precipitate was filtered off
14. washwashed three times with 30 ml of ether
15. dry with materialThe combined ether phases were dried over magnesium sulfate
16. distillationthe solvent was distilled off under normal pressure at about 65° bath temperature
17. distillationThe residue was distilled at about 80° bath temperature and 12 mmHg and there

ORD record

ord-0b304d8c9a0444179c5f9d9691fef13c

Source dataset

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04234490