Lithium Hydroxide → HCID 70158869, compound

HRID 278542Notes

Reaction equation

HRID 278542 reaction equation
COC(=O)[CH:4]([O:41][CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][O:43]1)[C:5](=[O:40])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@H:12]1[C@@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH2:15][C@@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[C@@H:13]1[CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].[Li+].[OH-]>C1COCC1>[Si:33]([O:32][CH2:31][C@H:13]1[C@H:14]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:15][C@H:16]([O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C@@H:12]1[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][C:5](=[O:40])[CH2:4][O:41][CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][O:43]1)([C:36]([CH3:39])([CH3:37])[CH3:38])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 70157489HCID 70157489, compound

Product 1

HCID 70158869HCID 70158869, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ketone of example 51 (60 mg, 0.086 mmol), THF (3 mL), and LiOH (0.3 mL, 1M in H2O, 0.34 mmol;) were combined and refluxed under N2 for 2 h. The THF was evaporated, the aqueous phase was extracted with CH2Cl2 (2×), and the combined organics were washed with brine and dried (Na2SO4) filtered and concentrated in vacuo. FCC (silica gel 1:4, EtOAc/hex) afforded the desired ketone (47 mg).

Workup

  1. temperaturerefluxed under N2 for 2 h
  2. customThe THF was evaporated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×)
  4. washthe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e9c365ee8954b66a8f24a868c41289e
Source dataset
uspto-grants-2002_03
Patent number
US06359181B1

Reaction notes

Loading…