Methanol → 4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid

HRID 24118Notes

Reaction equation

HRID 24118 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([CH:26]3[CH2:28][CH2:27]3)[C:15]3[O:22][C:19]4([CH2:21][CH2:20]4)[CH2:18][C:17]([CH3:24])([CH3:23])[C:16]=3[CH:25]=2)=[CH:6][C:5]=1[F:29].CO.[OH-].[Na+].O>C(#N)C>[CH:26]1([C:14]2[C:15]3[O:22][C:19]4([CH2:20][CH2:21]4)[CH2:18][C:17]([CH3:23])([CH3:24])[C:16]=3[CH:25]=[C:12]([C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[C:5]([F:29])[CH:6]=3)[CH:13]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 695484184-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester2×

Product 1

HCID 99303234-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following general procedure L and using 4-[(8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane]-6yl)ethynyl]-2-fluoro-benzoic acid methyl ester (Compound 53, 0.01 g, 0.047 mmol), 5 mL of methanol and 1M sodium hydroxide solution (2 mL) followed by preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase, the title compound was obtained as a solid (0.01 g, 56%).

Sources & evidence

ORD record
ord-2186b6e9f1814aff86e0a355537cf54c
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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