Acetic Acid → HCID 59300386, compound

HRID 2236553Notes

Reaction equation

HRID 2236553 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:20]([O:22][C:23](=O)[O:24]CC)[CH3:21].C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.C(O)(=O)C>O1CCCC1>[CH2:20]([O:22][C:23]([CH2:1][C:2]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:24])[CH3:21]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 59300324HCID 59300324, compoundHCID 178418339Butyllithium

Product 1

HCID 59300386HCID 59300386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-methyl-4-(2-morpholin-4-yl-ethoxy)-benzoic acid (3.58 g, 13.5 mmole) and diethylcarbonate (2.40 g, 20.4 mmole) in tetrahydrofuran (30 mL) is added dropwise to a solution of lithium diisopropylamide (30.0 mmole) at −78° C. (freshly prepared from diisopropylamine (3.04 g, 30.0 mmole) and n-butyllithium (18.8 mL of 1.6M in hexanes, 30.1 mmole) in tetrahydrofuran (20 mL)) over 15 minutes. This mixture is allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture is cooled with an ice bath then glacial acetic acid (3.1 mL, 54.0 mmole) is added dropwise. The tetrahydrofuran evaporated in vacuo and the mixture is then extracted with ethyl acetate (3×25 mL). The ethyl acetate layer is dried over sodium sulfate, filtered and evaporated. This is purified by HPLC (acetonitrile-water without trifluoroacetic acid and dried to give, 2.81 g, (61%), MS (ESI): m/z 338.1 (M+H).

Workup

  1. temperatureThe reaction mixture is cooled with an ice bath
  2. customThe tetrahydrofuran evaporated in vacuo
  3. extractionthe mixture is then extracted with ethyl acetate (3×25 mL)
  4. dry with materialThe ethyl acetate layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThis is purified by HPLC (acetonitrile-water without trifluoroacetic acid
  8. customdried
  9. customto give

Sources & evidence

ORD record
ord-50137fb5efe24d3aa62df022802ffc7d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…