Sodium Hydroxide → HCID 57144615, compound

HRID 1243206Notes

Reaction equation

HRID 1243206 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C@H:5]([O:7][Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6].[OH-].[Na+]>O1CCCC1CO>[C:21]([Si:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:7][C@H:5]([CH3:6])[CH2:4][C:3]([OH:25])=[O:2])([CH3:22])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12040185HCID 12040185, compound

Product 1

HCID 57144615HCID 57144615, compound

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Procedure

The protected ester (0.84 g, 2.36 mmol) was dissolved in 3:1 tetrahydrofuran-methanol and treated with aqueous sodium hydroxide (1.0 N, 3.0 mL, 3.00 mmol) at ˜42° C. overnight. The reaction was concentrated. The residue was partitioned between ethyl acetate and water and acidified with 1 N aqueous hydrochloric acid. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by flash chromatography (Biotage 40M, 20:80 ethyl acetate-hexanes) gave (R)-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid. (Yield 0.63 g, 69.9%).

Workup

  1. concentrationThe reaction was concentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (Biotage 40M, 20:80 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d1d4c9c44f8946f28e9365366daa0ef8
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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