Lithium Hydroxide → HCID 6928767, compound

HRID 349191Notes

Reaction equation

HRID 349191 reaction equation
CC1(C)COC(=O)[C@@H]1[C:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][C@@H:9]2[C:16]([O-:18])=[O:17].[OH-].[Li+]>O1CCCC1.O>[CH:8]12[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]1)[CH2:10][C@@H:9]2[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86598496HCID 86598496, compound

Product 1

HCID 6928767HCID 6928767, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of formula (VIIa) (Intermediate 3, 18.0 g, 67.7 mmol) was dissolved in tetrahydrofuran (100 mL) and the resulting solution cooled to 5–10° C. A solution of lithium hydroxide (7 g) in water (140 mL) was added slowly, maintaining the reaction temperature to below 25° C. and the mixture was stirred for 24 hours at room temperature, then concentrated in vacuo until most of tetrahydrofuran had been removed. Concentrated HCl was added drop-wise to adjust the pH to 2, water (60 mL) was added and the slurry stirred at 0–10° C. for one hour. The precipitate was isolated by filtration, and dried in a vacuum oven. The crude product of formula (IIIa) was used without any further purification (9.35 g, 90%).

Workup

  1. temperaturethe resulting solution cooled to 5–10° C
  2. temperaturemaintaining the reaction temperature to below 25° C.
  3. concentrationconcentrated in vacuo until most of tetrahydrofuran
  4. customhad been removed
  5. additionConcentrated HCl was added drop-wise
  6. additionwas added
  7. stirringthe slurry stirred at 0–10° C. for one hour
  8. customThe precipitate was isolated by filtration
  9. customdried in a vacuum oven
  10. customThe crude product of formula (IIIa) was used without any further purification (9.35 g, 90%)

Sources & evidence

ORD record
ord-effd6fc5206e4191851b0e5dbeefe1e4
Source dataset
uspto-grants-2007_02
Patent number
US07179813B2

Reaction notes

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