Methanol → [4-(8-Ethynyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-2-fluoro-phenyl]-acetic acid

HRID 898672Notes

Reaction equation

HRID 898672 reaction equation
C[O:2][C:3](=[O:34])[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]([C:23]#[C:24][Si](C)(C)C)[CH:22]=2)[O:19][C:18]([CH3:30])([CH3:29])[CH2:17][C:16]3([CH3:32])[CH3:31])=[CH:7][C:6]=1[F:33].CO.O1CCCC1.O.[OH-].[Li+]>O>[C:23]([C:21]1[CH:22]=[C:13]([C:12]#[C:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:34])=[O:2])=[C:6]([F:33])[CH:7]=2)[CH:14]=[C:15]2[C:20]=1[O:19][C:18]([CH3:29])([CH3:30])[CH2:17][C:16]2([CH3:32])[CH3:31])#[CH:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69212794HCID 69212794, compound2×

Product 1

HCID 10237512[4-(8-Ethynyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-2-fluoro-phenyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following general procedure K and using [2-fluoro-4-(2,2,4,4-tetramethyl-8-trimethylsilanylethynyl-chroman-6-ylethynyl)-phenyl]-acetic acid methyl ester (Compound 39, 0.11 g, 0.23 mmol), methanol, tetrahydrofuran, water and lithium hydroxide monohydrate followed by recrystallization from hot acetonitrile, the title compound was obtained as a pale yellow solid (0.045 g, 50%).

Workup

  1. customfollowed by recrystallization from hot acetonitrile

Sources & evidence

ORD record
ord-41ea9e772268457f92ec3345e86f297e
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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