Hydrochloric Acid → HCID 57983925, compound

HRID 1869117Notes

Reaction equation

C([Li])CCC.[F:6][C:7]([F:15])([F:14])[CH:8]([OH:13])[C:9]([F:12])(F)[F:10].[CH:16]12[CH2:22][CH:19]([CH:20]=[CH:21]1)[CH2:18][CH:17]2[C:23]([O:25][CH2:26][C:27](=[O:29])[CH3:28])=[O:24].Cl.[O:31]1CCCC1>CCCCCC>[CH:16]12[CH2:22][CH:19]([CH:20]=[CH:21]1)[CH2:18][CH:17]2[C:23]([O:25][CH2:26][C:27]([CH3:28])([OH:29])[C:9]([F:12])([F:10])[C:8]([OH:31])([OH:13])[C:7]([F:15])([F:14])[F:6])=[O:24]

Participants

Conditions

Temperature: 5 °C

Procedure

In a nitrogen atmosphere at 5° C., 100 ml of 1.6M n-butyllithium in hexane was added to a mixture of 21.7 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 120 g of tetrahydrofuran. The mixture was stirred at 5° C. for 1 hour. Then a dilution of 22.8 g of 2-oxopropyl 5-norbornene-2-carboxylate in 30 g of tetrahydrofuran was added at 5° C. The mixture was stirred for 15 hours, after which dilute hydrochloric acid was added for quenching and neutralization. This was followed by conventional aqueous work-up and recrystallization from hexane for purification, collecting 24.6 g of 2-methyl-3,3,5,5,5-pentafluoro-2,4,4-trihydroxypentyl 5-norbornene-2-carboxylate (yield 58%).

Workup

stirringThe mixture was stirred for 15 hours
customfor quenching
customThis was followed by conventional aqueous work-up and recrystallization from hexane for purification

Sources & evidence

ORD record: ord-0edd60dcc8004f189c8c27fed10880ed
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638256B2

Reaction notes

Loading…