Etodolac → HCID 10891051, compound

HRID 901055

Reaction equation

HRID 901055 reaction equation
[CH3:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]3[CH2:12][CH2:13][O:14][C:15]([CH2:18][C:19](O)=[O:20])([CH2:16][CH3:17])[C:10]=3[NH:9][C:8]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:16]([C:15]1([CH2:18][CH2:19][OH:20])[C:10]2[NH:9][C:8]3[C:7]([C:11]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:2][CH3:1])[CH3:17]

Participants

4

Reactant 2

HCID 3308EtodolacHCID 21226445Aluminium lithium hydride

Product 1

HCID 10891051HCID 10891051, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of etodolac (2.0 g, 6.97 mmol) in dry THF (5 mL) was added dropwise to 1M LiAlH4 in THF (10.5 mL, 10.5 mmol, 1.5 eq) over five minutes and stirred at room temperature overnight under argon. The resulting mixture was then slowly quenched with EtOAc and poured over water to form an emulsion. The emulsion was filtered, and the aqueous layer was separated and extracted twice with EtOAc. The three organic phases were combined, washed with brine, dried with Na2SO4, concentrated, and purified by column chromatography using 50:50:EtOAc:Hexane to give a yellow oil (1.87 g, 98%): 1HNMR (CDCl3, δ TMS): 0.95 (t, 3H), 1.36 (t, 3H), 1.96 (m, 2H), 2.14 (m, 2H), 2.68 (br, OH), 2.81 (m, 2H), 2.83 (q, 2H), 3.70 (m, 2H), 4.07 (m, 2H), 7.02-7.39 (m, 3H, Ar—H), 7.74 (br, 1H, NH). MS+: m/z 296 (MNa+). MS−: m/z 308 (MCl−), 272 ([M−H]−).

Workup

  1. customThe resulting mixture was then slowly quenched with EtOAc
  2. additionpoured over water
  3. customto form an emulsion
  4. filtrationThe emulsion was filtered
  5. customthe aqueous layer was separated
  6. extractionextracted twice with EtOAc
  7. washwashed with brine
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-59df60ed67b34d2f9ddb28de47bdaa95
Source dataset
uspto-grants-2008_04
Patent number
US07361680B2

Linked notes

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