Carbon Dioxide → [4-(8-Ethyl-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl]acetic acid

HRID 1936057Notes

Reaction equation

HRID 1936057 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]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.O1[CH2:23][CH2:22][CH2:21][CH2:20]1.[C:24]([Li])(C)(C)[CH3:25].[CH3:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:34](=[O:36])=[O:35]>CCCCCC.C(OCC)(=O)C>[CH2:24]([C:4]1[CH:3]=[C:2]([C:29]#[C:30][C:31]2[CH:20]=[CH:21][C:22]([CH2:23][C:34]([OH:36])=[O:35])=[CH:33][CH:32]=2)[CH:15]=[C:6]2[C:5]=1[O:12][C:9]([CH3:11])([CH3:10])[CH2:8][C:7]2([CH3:13])[CH3:14])[CH3:25]

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 10156384[4-(8-Ethyl-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl]acetic 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-b266921574064fc383de6062fa849f34
Source dataset
uspto-grants-2002_05
Patent number
US06387951B1

Reaction notes

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