Lithium hydroxide, monohydrate → HCID 71255648, compound

HRID 1481274Notes

Reaction equation

HRID 1481274 reaction equation
O.[OH-].[Li+].[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]>C1COCC1.CO.O>[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71254747HCID 71254747, compound

Product 1

HCID 71255648HCID 71255648, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide monohydrate (5.67 g, 135 mmol) was added to a solution of 5A (11.4 g, 45.0 mmol) in THF (120 mL), MeOH (120 mL) and H2O (40.0 mL). The above mixture was then heated to 50° C. for 1 h. After 1 h, the heating was reduced to rt and stirring was continued for overnight. To the reaction mixture was then added H2O (50 mL) and the organics were concentrated. The remaining aqueous layer was made acidic with 1.0 N HCl solution to precipitate out the solids. The solids were collected by filtration, washed with H2O and dried under vacuum overnight to give 5B. 1H NMR (400 MHz, DMSO-d6) δ 13.68 (br. s., 1H), 8.36 (d, J=1.5 Hz, 1H), 8.25 (dd, J=8.1, 1.3 Hz, 1H), 7.88 (d, J=8.1 Hz, 1H), 6.38 (s, 1H), 4.05-3.89 (m, 4H) ppm.

Workup

  1. customwas reduced to rt
  2. waitwas continued for overnight
  3. concentrationadded H2O (50 mL) and the organics were concentrated
  4. customto precipitate out the solids
  5. filtrationThe solids were collected by filtration
  6. washwashed with H2O
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-364977f772ab4bfe9d353e92471b4210
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

Loading…