Ethyl Acetate → HCID 12083031, compound

HRID 1168506Notes

Reaction equation

HRID 1168506 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH:11]=[C:12]([C:18]([O:20]CC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14].CCOC(C)=O>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[CH3:1][C:2]1([CH3:23])[N:3]2[C:4]3[C:5]([C:18](=[O:20])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11]2)=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:10]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 12083030HCID 12083030, compound

Product 1

HCID 12083031HCID 12083031, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Diethyl 2-((2,2-dimethyl-2,3-dihydro-1H-indol-1-yl)methylene)malonate (Preparation 11, 3.14 g) is dissolved in Eaton's Reagent (3.5 mL) and slowly heated to 100° C. The reaction is cooled and poured into EtOAc (350 mL). The separated organic layer is washed with water (2×200 mL). The aqueous extracts are extracted further with CH2Cl2 (2×100 mL). The organic extracts are washed with brine and dried over MgSO4, filtered and concentrated to a brown oil which is purified by chromatography over silica gel, eluting with 5% methanol in CH2Cl2 to give 2.3 g (85%) of the title compound as a pale yellow oil that slowly crystallizes. Physical characteristics: M.p. 117-119° C.; 1H NMR (DMSO-d6) δ8.73, 7.83, 7.61, 7.41, 4.22, 3.41, 1.63, 1.29; IR (diffuse reflectance) 1933, 1677, 1640, 1624, 1601, 1544, 1459, 1367, 1310, 1213, 1176, 1144, 1032, 773, 757 cm−1; MS (EI) m/z 271 (M+). Anal. Found: C, 70.48; H, 6.36; N, 5.12.

Workup

  1. temperatureThe reaction is cooled
  2. washThe separated organic layer is washed with water (2×200 mL)
  3. extractionThe aqueous extracts are extracted further with CH2Cl2 (2×100 mL)
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a brown oil which
  8. customis purified by chromatography over silica gel
  9. washeluting with 5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-b1ec549c25364852a49781ba4a24ac8c
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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