Carbon Dioxide → HCID 22475123, compound

HRID 2103109Notes

Reaction equation

[F:1][C:2]1[C:10]2[O:9][C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CN(CCN(C)C)C.C([Li])CCC.[C:36](=[O:38])=[O:37]>C1COCC1.O>[F:1][C:2]1[C:10]2[O:9][C:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:36]([OH:38])=[O:37]

Participants

Conditions

Temperature: -78 °C

Procedure

4-Fluoro-2,2-diphenyl-benzo[1,3]dioxole (5.8 g, 20 mmol) were dissolved in THF (40 ml). The reaction was cooled to −78° C. under argon. TMEDA (2.9 ml, 20 mmol) was added followed by n-butyl lithium (12.5 ml, 1.6 N in hexane) dropwise. The reaction was stirred at −78° C. for 2 hours. Carbon dioxide (20 g) was added at that temperature. The reaction was allowed to warm to 0° C. and poured into water (80 ml). The reaction was extracted twice with ethyl acetate. The aqueous layer was neutralized with 1N aqueous HCl solution, extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtered. The solvent was evaporated and the residue suspended in n-hexane, stirred for 10 minutes and the product was filtered off to yield the acid as a white solid (4.0 g, 60%). m.p.: 189-191° C.

Workup

temperatureto warm to 0° C.
extractionThe reaction was extracted twice with ethyl acetate
extractionextracted twice with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customThe solvent was evaporated
stirringstirred for 10 minutes
filtrationthe product was filtered off

Sources & evidence

ORD record: ord-a37744d7a70445e6a296f66f47469d2b
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576088B2

Reaction notes

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