Lithium Hydroxide → HCID 58291968, compound

HRID 1944724Notes

Reaction equation

HRID 1944724 reaction equation
C([O:3][C:4]([C:6]1([OH:20])[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].C1COCC1>CO>[C:16]([Si:13]([CH3:15])([CH3:14])[O:12][CH:9]1[CH2:10][CH2:11][C:6]([OH:20])([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58291838HCID 58291838, compound2×

Product 1

HCID 58291968HCID 58291968, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-cyclohexanecarboxylic acid ethyl ester (Intermediate 78, 1.35 g) was hydrolyzed to an acid by adding it to 45 ml of a solution of 1M LiOH in 1:1 THF:MeOH: at room temperature. The pH was adjusted to 3 and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated to give the title compound. MS MH+ 275.4

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6875917fdc0e4c6c9fedae3a6dffe0e1
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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