Trichlorofluoromethane → (nBu)3P CCl3F

HRID 640762Notes

Reaction equation

C(OC([C@@H](N1C(=O)CC(C=O)C1)CC)=O)(C)(C)C.[C:19]([Cl:23])([Cl:22])([Cl:21])[F:20].[P:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28].[PH4+].[OH-].[Na+]>>[P:24]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:25][CH2:26][CH2:27][CH3:28].[C:19]([F:20])([Cl:23])([Cl:22])[Cl:21]

Participants

Reactant 5

HCID 6389Trichlorofluoromethane

HCID 13831Tributylphosphine

HCID 14798Sodium Hydroxide

HCID 5460504Phosphonium

HCID 183461161-[(1S)-1-(tertbutoxycarbonyl)propyl]-5-oxo-3-pyrrolidinecaboxaldehyde

Product 1

HCID 131725019(nBu)3P CCl3F

Procedure

Alternatively to §6.2.3., halovinyl derivatives can be obtained by Wittig olefination of the 1-[(1S)-1-(tertbutoxycarbonyl)propyl]-5-oxo-3-pyrrolidinecarboxaldehyde 396 in the presence of a phosphine and an halogenomethane. For example of 2-(2-oxo-4-(2-(Z)-fluorovinyl)-1-pyrrolidinyl)butanoic acid 2,2-(dimethyl)ethyl ester is obtained from aldehyde 396 by successive reaction with CFCl3 and n-Bu3P followed by dephosphorylation of the intermediate vinylic phosphonium by NaOH.

Sources & evidence

ORD record: ord-56462a5c199f4d8e947c94389b29e5d5
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692028B2

Reaction notes

Loading…