Carbon Dioxide → spiro[2H-1-benzopyran-2,1'-cyclopropane]-6-carboxylic acid

HRID 427838Notes

Reaction equation

HRID 427838 reaction equation
Br[C:2]1[CH:3]=[C:4](C2CC2)[C:5]2[O:12][C:9]3([CH2:11][CH2:10]3)[CH2:8][C:7](C)(C)[C:6]=2[CH:15]=1.O1CCCC1.C([Li])(C)(C)C.CCCCC.[C:34](=[O:36])=[O:35]>CCCCCC.C(OCC)(=O)C>[C:9]12([CH:8]=[CH:7][C:6]3[CH:15]=[C:2]([C:34]([OH:36])=[O:35])[CH:3]=[CH:4][C:5]=3[O:12]1)[CH2:10][CH2:11]2

Participants

8

Reactant 5

HCID 280Carbon Dioxide2×HCID 8003PentaneHCID 8028TetrahydrofuranHCID 225689116-Bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]2×HCID 178418306HCID 178418306, compound

Product 1

HCID 22568970spiro[2H-1-benzopyran-2,1'-cyclopropane]-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure R and using 6-bromo-8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane] (Intermediate 42, 0.45 g, 1.48 mmol), anhydrous tetrahydrofuran (5 mL), 1.7M solution of tert-butyl lithium solution in pentane (1.74 mL, 2.96 mmol) and carbon dioxide generated from dry ice, followed by flash column chromatography over silica gel (230-400 mesh) using 50% ethyl acetate in hexane as the eluent, the title compound was obtained as a white solid (0.34 g, 85%).

Sources & evidence

ORD record
ord-1c08faeceb0441ca8e0c4d52c2833bc4
Source dataset
uspto-grants-2001_11
Patent number
US06313107B1

Reaction notes

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