Sodium Hydroxide → HCID 11500391, compound

HRID 1443062Notes

Reaction equation

HRID 1443062 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH:12]([CH:19]1[O:24][CH2:23][C:22](=O)[NH:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>C1(C)C=CC=CC=1>[NH:21]1[CH2:22][CH2:23][O:24][CH:19]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][OH:3])[CH2:20]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16684438Red-AlHCID 68545416HCID 68545416, compound

Product 1

HCID 11500391HCID 11500391, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[(5-Oxo-morpholin-2-yl)-phenyl-methoxy]-benzoic acid ethyl ester (0.66 g) was taken up in 10 mL toluene, and cooled to 0 C for the addition of Red-Al (2.8 mL, 5 equiv). The mixture was allowed to warm to room temperature. After 12 h, 2 mL 2 N NaOH was added, and the mixture was stirred at room temperature for 30 min, extracted with toluene (2×5 mL). The organics were combined, dried over MgSO4, filtered and concentrated. The residual oil was taken up in DCM, and pumped onto silica, and purified by MPLC in DCM/MeOH+0.1 NH4OH. Fractions containing the desired compound were combined and concentrated. 0.287 g of [2-(Morpholin-2-yl-phenyl-methoxy)-phenyl]-methanol as a pale yellow oil (51% yield, M+1=300.1).

Workup

  1. extractionextracted with toluene (2×5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by MPLC in DCM/MeOH+0.1 NH4OH
  6. additionFractions containing the desired compound
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8a7b66f77cb041e7a9695cb543ff90b1
Source dataset
uspto-grants-2010_02
Patent number
US07659394B2

Reaction notes

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