Sodium Hydroxide → HCID 53393312, compound

HRID 1777794Notes

Reaction equation

HRID 1777794 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:9][C@H:8]1[C:10](OCC)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@H:7]1[CH2:9][C@H:8]1[CH2:10][OH:11]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 66837013HCID 66837013, compound

Product 1

HCID 53393312HCID 53393312, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 13-3 (751 mg, 3.93 mmol) in THF (20 mL) was cooled to 0° C. and treated slowly with lithium aluminum hydride (3.93 mL, 3.93 mmol, 1 M solution in THF). The solution was warmed to room temperature and stirred for 20 min. The reaction mixture was then recooled to 0° C. and treated sequentially dropwise with 0.15 mL of water, 0.15 ml of 15% NaOH, and 0.45 mL of water. Sodium sulfate was added to the mixture. After stirring at room temperature for 10 min, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to afford the title compound as a pale yellow oil. The material was sufficiently pure to use in the subsequent step without further purification. LC/MS: m/z (M+H)=150.1.

Workup

  1. customwas then recooled to 0° C.
  2. stirringAfter stirring at room temperature for 10 min
  3. filtrationthe mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cb1be2621f1e49749583b04c88b58dbb
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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