Lithium Hydroxide → HCID 178525769, compound

HRID 1631436Notes

Reaction equation

HRID 1631436 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178472438HCID 178472438, compound

Product 1

HCID 178525769HCID 178525769, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 13B (6.8 g, 19.35 mmol) in THF (25 mL) and water (5.00 mL) was treated LiOH. H2O (4.06 g, 97 mmol) and stirred at room temperature over a weekend. The reaction mixture was concentrated to halfvolume and acidified with 1.0N HCl carefully to ˜pH6. The resulting white solid was collected by filtration and air dried to provide 13C (5.0 g, 80% yield). MS (ES): m/z=324.3 [M+H]+. 1H NMR (400 MHz, CDCl3) δ ppm 7.17-7.47 (m, 10H); 3.64 (s, 4H); 2.46-2.61 (m, 1H); 2.17-2.33 (m, 1H); 1.92-2.15 (m, 4H); 1.28-1.52 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated to halfvolume
  2. filtrationThe resulting white solid was collected by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-20bd8970cf3d459f9f8af1a6ff386f71
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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