Sodium Hydroxide → HCID 11638729, compound

HRID 1243194Notes

Reaction equation

HRID 1243194 reaction equation
[C:1]([Si:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:6][CH2:7][C@@H:8]([CH3:13])[C:9]([O:11]C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCCC1CO>[C:1]([Si:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:6][CH2:7][C@@H:8]([CH3:13])[C:9]([OH:11])=[O:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11121845HCID 11121845, compound

Product 1

HCID 11638729HCID 11638729, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

Methyl (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionate (2.42 g, 7.05 mmol) was dissolved in 3:1 tetrahydrofuran-methanol (24 mL) and saponified with aqueous sodium hydroxide (1.0 N, 7.9 mL, 7.90 mmol) at 40° C. for 3 hours and then overnight at ambient temperature. The reaction mixture was concentrated. The residue was dissolved in ethyl acetate and then acidified with 1.0 N aqueous hydrochloric acid (˜8 mL). The organic phase was washed with brine (3×), dried over anhydrous sodium sulfate and concentrated. Purification by flash chromatography (Biotage 40L, 20:80 ethyl acetate-hexanes) gave (R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid as an oil that solidified to a tacky white solid. (Yield 1.60 g, 67.6%).

Workup

  1. customovernight
  2. customat ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washThe organic phase was washed with brine (3×)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customPurification by flash chromatography (Biotage 40L, 20:80 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-067f3a3813fb4d31a39059a92f45506b
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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