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

HRID 1861374Notes

Reaction equation

HRID 1861374 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:27]3[CH2:29][CH2:28]3)[C:16]3[O:23][C:20]4([CH2:22][CH2:21]4)[CH2:19][C:18]([CH3:25])([CH3:24])[C:17]=3[CH:26]=2)=[CH:7][C:6]=1[F:30].CO.[OH-].[Na+]>ClCCl>[CH:27]1([C:15]2[C:16]3[O:23][C:20]4([CH2:22][CH2:21]4)[CH2:19][C:18]([CH3:25])([CH3:24])[C:17]=3[CH:26]=[C:13]([C:12]#[C:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:31])=[O:2])=[C:6]([F:30])[CH:7]=3)[CH:14]=2)[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 695487094-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[-2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzeneacetic acid methyl ester2×

Product 1

HCID 98225114-[(8-Cycloproply-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzeneacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following general procedure L and using 4-[(8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzeneacetic acid methyl ester (Compound 49, 0.096 g, 0.23 mmol), 5 mL of methanol and 1M sodium hydroxide solution (2 mL) followed by flash column chromatography over silica gel (230-400 mesh) using 15% methanol in dichloromethane as the eluent, the title compound was obtained as a solid (0.093 g, 100%).

Sources & evidence

ORD record
ord-1959011f1f39400d8a591dba29b96da9
Source dataset
uspto-grants-2003_03
Patent number
US06531599B2

Reaction notes

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