Methanol → [4-(8-Cyclopropyl-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)phenyl]acetic acid

HRID 278674Notes

Reaction equation

HRID 278674 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([CH:23]4[CH2:25][CH2:24]4)[CH:22]=2)[O:19][C:18]([CH3:27])([CH3:26])[CH2:17][C:16]3([CH3:29])[CH3:28])=[CH:7][CH:6]=1.CO.[OH-].[Na+].O>C(#N)C>[CH:23]1([C:21]2[CH:22]=[C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:30])=[O:2])=[CH:10][CH:9]=3)[CH:14]=[C:15]3[C:20]=2[O:19][C:18]([CH3:26])([CH3:27])[CH2:17][C:16]3([CH3:29])[CH3:28])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 69547849[4-(8-Cyclopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]acetic acid methyl ester2×

Product 1

HCID 10134883[4-(8-Cyclopropyl-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following general procedure L and using [4-(8-cyclopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl) phenyl]acetic acid methyl ester (Compound 35, 0.137 g, 0.30 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 (0.11 g, 80%).

Sources & evidence

ORD record
ord-c59e2224824e4655bfe48d95c09db113
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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