Water → HCID 10237257, compound

HRID 898670Notes

Reaction equation

HRID 898670 reaction equation
C[O:2][C:3](=[O:33])[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][CH:6]=1.O1CCCC1.O.O.[OH-].[Li+]>CO>[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:33])=[O:2])=[CH:6][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 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69215925HCID 69215925, compound2×

Product 1

HCID 10237257HCID 10237257, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [4-(2,2,4,4-tetramethyl-8-trimethylsilanylethynyl-chroman-6-ylethynyl)-phenyl]-acetic acid methyl ester (Compound 38, 0.13 g, 0.28 mmol) in a mixture of methanol (3 mL), tetrahydrofuran (3 mL) and water (1.5 mL) was treated with lithium hydroxide monohydrate (0.13 g, 3.1 mmol) and the resulting reaction mixture was stirred at ambient temperature for 2.5 h. The volatiles were distilled off in vacuo and the residue was diluted with water and saturated aqueous ammonium chloride solution and extracted with ethyl acetate (×3). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a white solid (0.078 g, 74%).

Workup

  1. customthe resulting reaction mixture
  2. distillationThe volatiles were distilled off in vacuo
  3. additionthe residue was diluted with water and saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-562fd6079c7b45dbbca118e53ba2d194
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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