Ethyl Acetate → HCID 21104829, compound

HRID 1354236Notes

Reaction equation

HRID 1354236 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:21])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[O:19][CH3:20])=[N:6][CH:7]=1.CN1[C:27](=[O:28])[CH2:26][CH2:25]C1.[CH3:29][CH2:30]OC(C)=O>CCCCCC>[CH2:29]([CH:27]([O:28][C:2]1[CH:3]=[C:4]([CH3:21])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[O:19][CH3:20])=[N:6][CH:7]=1)[CH2:26][CH3:25])[CH3:30]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 21104834HCID 21104834, compound

Product 1

HCID 21104829HCID 21104829, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

Compound 42 (3.62 g, 10 mmol) is added to a solution of sodium 3-pentoxide in NMP (1M, 30 ml, 30 mmol). The resulting mixture is heated to 120° C. for 2.5 h, and then cooled to room temperature, diluted with 50% EtOAc in hexane, washed with water, brine, dried, filtered and evaporated. The crude product is purified by chromatography (eluted with 6% EtOAc in hexane) to give the product as colorless oil. 1H NMR (CDCl3) δ 0.98 (t, J=7.6 Hz, 6H), 1.72 (m, 4H), 2.15 (s, 3H), 3.77 (s, 3H), 4.17 (m, 1H), 6.79 (s, 1H), 6.91 (dd, 1H), 7.07 (d, J=1.6 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 8.18 (d, J=1.6 Hz, 1H). LCMS 370.2 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water, brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by chromatography (eluted with 6% EtOAc in hexane)

Sources & evidence

ORD record
ord-0decabb667db4e6b8303cb0d86512db5
Source dataset
uspto-grants-2007_05
Patent number
US07223778B2

Reaction notes

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