2-Morpholinoethanol → HCID 69659280, compound

HRID 1829064Notes

Reaction equation

HRID 1829064 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20][C:21]([OH:23])=[O:22])[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[Li]CCCC.C(Cl)(=O)C(Cl)=O.O[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C1COCC1.CCCCCC>[N:38]1([CH2:37][CH2:36][O:22][C:21](=[O:23])[CH2:20][CH:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11](=[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[NH:3][C:2]3=[O:1])[O:12]2)[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 611632-MorpholinoethanolHCID 65578Oxalyl chlorideHCID 69659233HCID 69659233, compoundHCID 178418339Butyllithium

Product 1

HCID 69659280HCID 69659280, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a slurry of [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (100 mg, 0.32 mmol) in THF (4.0 ml) at room temperature was added 2.5M n-BuLi in hexane (13611), and the reaction was stirred for 10 minutes. After the reaction was cooled to 0° C., oxalyl chloride (163 μl, 0.32 mmol) was added. After stirring for 20 minutes, 4-(2-hydroxyethyl)morpholine (118 μl, 0.976 mmol) was added. The reaction was stirred for 5 minutes at 0° C., and then at room temperature for 20 minutes. The reaction was partitioned between EtOAc and saturated NaHCO3. The EtOAc layer was washed with brine, dried with anhydrous Na2SO4 and rotary evaporated to afford an orange oil. The orange oil was chromatographed through silica gel column, eluted with CHCl3, to give [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid 2-morpholin-4-yl-ethyl ester as a yellow foam (43 mg, 32%).

Workup

  1. stirringAfter stirring for 20 minutes
  2. stirringThe reaction was stirred for 5 minutes at 0° C.
  3. waitat room temperature for 20 minutes
  4. customThe reaction was partitioned between EtOAc and saturated NaHCO3
  5. washThe EtOAc layer was washed with brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customrotary evaporated
  8. customto afford an orange oil
  9. customThe orange oil was chromatographed through silica gel column
  10. washeluted with CHCl3

Sources & evidence

ORD record
ord-ea64a15b5415499892bd653af17c7b6d
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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