Lithium Hydroxide → HCID 25056534, compound

HRID 2101778Notes

Reaction equation

HRID 2101778 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C@@H:28]([CH:35]=[CH2:36])[CH2:29][C:30]([O:32]CC)=[O:31])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Li+].[OH-]>C1COCC1.CO>[CH3:4][C:2]([C:5]1[C:10]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[CH:9][C:8]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C@@H:28]([CH:35]=[CH2:36])[CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57672395HCID 57672395, compound

Product 1

HCID 25056534HCID 25056534, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 20.3 (0.040 g, 0.082 mmol) in THF/MeOH (2/1) (1.5 mL) was added a 1 M solution of LiOH (0.50 mL, 0.50 mmol). The resulting mixture was stirred overnight at 23° C., quenched with excess 1 N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The crude residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes) to afford a 20 (0.022 g, 58% yield). MS ESI (neg.) m/e: 461.2 (M−H)+.

Workup

  1. customquenched with excess 1 N HCl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3ef2b6859e04411db17ec21ce60f8ec3
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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