Methoxymethyl-triphenylphosphonium chloride → 1024683-61-1

Temperature

-78 °C

To a stirred suspension of methoxymethyl triphenylphosphonium chloride (13.8 g, 40 mmol) in dry THF (80 ml) is added dropwise a solution of lithium diisopropylamide (24.4 ml, 44 mmol, 1.8 M in hexane/THF/ethylbenzene), at 0-5° C. The resulting reaction mixture is stirred for 30 minutes and then cooled to −78° C. At this temperature, a solution of 4-benzyloxy-cyclohexanone (6.1 g, mmol) in tetrahydrofuran (30 ml) is added over a period of 30 minutes. Once the addition is completed the reaction mixture is stirred at −78° C. for 1 hour and then allowed to warm to room temperature and stirred overnight. The reaction mixture is then diluted to pH=2 with a 2N aqueous solution of hydrochloric acid and stirred for 3 hours at room temperature. The reaction was diluted with water and extracted with ethyl acetate (2×100 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is purified by flash chromatography to give 4-benzyloxy-cyclohexanecarbaldehyde (5.7 g).

1. customat 0-5° C
2. customThe resulting reaction mixture
3. additionOnce the addition
4. stirringis stirred at −78° C. for 1 hour
5. temperatureto warm to room temperature
6. stirringstirred overnight
7. stirringstirred for 3 hours at room temperature
8. extractionextracted with ethyl acetate (2×100 ml)
9. dry with materialThe combined organic extracts are dried over magnesium sulphate
10. filtrationfiltered
11. customevaporated under reduced pressure
12. customThe residue is purified by flash chromatography

ORD record

ord-4327da5e0600457db7b8ad48845ee6d4

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791303B2