Sodium Hydroxide → HCID 55288000, compound

(±)-(3-Hydroxy-5-methyl-hex-4-enyl)carbamic acid methyl ester (38.9 g, 219 mmol) dissolved in tetrahydrofuran (150 mL) was added drop-wise to a refluxing solution of LiAlH4 (1M in tetrahydrofuran, 232 mL) maintaining reflux. After refluxing for 2 h. the mixture was cooled on an ice bath and 15% aq. sodium hydroxide (50 mL) was added drop-wise until a white precipitate separated out. The precipitate was filtrated and washed with tetrahydrofuran (2×200 mL), dichloromethane (2×200 mL) and diethylether (2×200 mL). The combined washes were evaporated. The resulting oil was redissolved in diethylether, dried (sodium sulfate), filtered and evaporated to give the crude product (29.5 g, 100%) as a yellow oil. The crude product was used without further purification.

1. temperaturemaintaining
2. temperaturereflux
3. temperatureAfter refluxing for 2 h. the mixture
4. temperaturewas cooled on an ice bath
5. customseparated out
6. filtrationThe precipitate was filtrated
7. washwashed with tetrahydrofuran (2×200 mL), dichloromethane (2×200 mL) and diethylether (2×200 mL)
8. customThe combined washes were evaporated
9. dissolutionThe resulting oil was redissolved in diethylether
10. dry with materialdried (sodium sulfate)
11. filtrationfiltered
12. customevaporated

ORD record

ord-db7b13468e104cfa9de52c726b30980f

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973082B2