Lithium Hydroxide → HCID 25057310, compound

HRID 2101776Notes

Reaction equation

HRID 2101776 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]=[CH:36]/[CH2:37][CH3:38])[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]=[CH:36]/[CH2:37][CH3:38])[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 57672430HCID 57672430, compound

Product 1

HCID 25057310HCID 25057310, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 18.3 (0.040 g, 0.077 mmol) in THF/MeOH (2/1) (1.5 mL) was added 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 residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes) to afford 18 (0.0130 g, 34% yield). MS ESI (neg.) m/e: 489.2 (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 residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a70da02cc7d3448f9870d69aa0db7d34
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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