Sodium Hydroxide → HCID 19013525, compound

HRID 1729099Notes

Reaction equation

HRID 1729099 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[N:6]=1)=O.[OH-].[Na+]>C1COCC1.C1(C)C=CC=CC=1>[OH:2][CH2:3][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54438328HCID 54438328, compound

Product 1

HCID 19013525HCID 19013525, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred suspension of ester of Step 1 (31.0 g, 94 mmol) in dry THF (600 mL) cooled at 5° C. and under nitrogen was added dropwise and at this temperature a solution of Red-A1 (sodium dihydro-bis (2-methoxyethoxy)aluminate--70% in toluene) (34 mL, 114 mmol) in dry THF (30 mL). After stirring 2 hours at 5° C., and then 1 hour at room temperature the mixture was cooled at 10° C. and treated dropwise with 2N NaOH (100 mL) to effect hydrolysis of the intermediate complex. The organic phase was separated and the solvent in vacuo evaporated. The residue was chromatographed over silica gel using MeOH/CH2Cl2 5:95 (v/v) as eluant to give the required alcohol (13.5 g, 54%) as a yellow oil which solidified upon standing, m.p. 95°-98 ° C.

Workup

  1. temperature1 hour at room temperature the mixture was cooled at 10° C.
  2. customhydrolysis of the intermediate complex
  3. customThe organic phase was separated
  4. customthe solvent in vacuo evaporated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-842f999d12754fc8859934170e5a184c
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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