Tetrahydrofuran → HCID 86607630, compound

HRID 1990828Notes

Reaction equation

HRID 1990828 reaction equation
C(O[C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([NH:14][C:15](=[O:17])[CH3:16])=[C:7]([O:18][CH2:19][CH3:20])[CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1C[O:31]CC1>O=[Mn]=O>[C:15]1(=[O:17])[N:14]([C:8]2[C:7]([O:18][CH2:19][CH3:20])=[CH:6][C:5]([CH:4]=[O:21])=[CH:10][C:9]=2[O:11][CH2:12][CH3:13])[C:16]1=[O:31]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 68701089HCID 68701089, compound

Product 1

HCID 86607630HCID 86607630, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

To a solution of 4-acetylamino-3,5-diethoxy-benzoic acid ethyl ester (1.0 g, 3.56 mmol, 1.0 equiv; [CAS RN 142955-43-9] prepared as described in EP 488 861 A1, Rhone Poulenc Chimie) in anhydrous THF (40 mL) was added lithium aluminium hydride (0.283 g, 7.47 mmol, 2.1 equiv) and the reaction mixture stirred at rt for 2 h. The crude reaction mixture was filtered over Hyflo Super Cel, the filtrate extracted with ethyl acetate (3×50 mL) and the combined organic phases dried over MgSO4 providing 0.58 g (64%) of the benzyl alcohol. The crude reaction product (0.39 g, 1.54 mmol, 1.0 equiv) was dissolved in THF (20 mL) and activated MnO2 (1.34 g, 15.40 mmol, 10.0 equiv) was added. After stirring at 60° C. for 2 h, the reaction mixture was filtered over Hyflo Super Cel and the solvent removed by evaporation under reduced pressure providing 0.35 g (90%) of the title compound. MS (ISP): 252.1 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered over Hyflo Super Cel
  3. extractionthe filtrate extracted with ethyl acetate (3×50 mL)
  4. dry with materialthe combined organic phases dried over MgSO4 providing 0.58 g (64%) of the benzyl alcohol
  5. stirringAfter stirring at 60° C. for 2 h
  6. filtrationthe reaction mixture was filtered over Hyflo Super Cel
  7. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-990b4b9d40ac4829b86c036e65ac2c92
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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