Sodium Hydroxide → HCID 22184655, compound

HRID 1795068Notes

Reaction equation

HRID 1795068 reaction equation
[CH:1]([Si:4]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:9][CH2:8]1)([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[CH:21]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:18]([CH3:20])[CH3:19])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([CH2:13][C:14]([OH:16])=[O:15])[CH2:11][CH2:12]1)([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22184672HCID 22184672, compound

Product 1

HCID 22184655HCID 22184655, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.8 g (25.7 mmol) of methyl ester from Step E in 50 mL of THF and 50 mL of methanol was added 25 mL (24.9 mmol) of 1 N aqueous sodium hydroxide. The resultant mixture was stirred at room temperature overnight, and the solvent was removed under vacuum. The residue was diluted with ice water, and then acidified with 1 N aqueous hydrochloric acid. The mixture was extracted with three portions of ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, and concentrated to provide a quantitative yield of the title compound. 1H NMR (500 MHz, CDCl3) δ 3.58 (d, 0.6H, J=6.7 Hz), 3.39 (d, 1.4H, J=6.2 Hz), 2.38 (d, 0.6H, J=4.4 Hz), 2.24 (d, 1.4H, J=3.9 Hz), 1.82–1.60 (m, 4H), 1.54 (m, 1H), 1.45 (m, 1H), 1.1–1.05 (m, 23H).

Workup

  1. customthe solvent was removed under vacuum
  2. additionThe residue was diluted with ice water
  3. extractionThe mixture was extracted with three portions of ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-92f8aa81ed404d20ad238315f5fb53d1
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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