Hexane → HCID 178424612, compound

HRID 1802447Notes

Reaction equation

HRID 1802447 reaction equation
[CH3:1][C:2]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)([CH3:6])[C:3](=[NH:5])[CH3:4].[C:12]1([CH3:29])[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20])[CH:13]=1.CCCCCC>C(OCC)C.COCCOCCOC>[S:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:2]([C:3]1[N:5]=[C:24]([OH:25])[C:18]([C:14]2[CH:13]=[C:12]([CH3:29])[CH:17]=[CH:16][CH:15]=2)=[C:19]([OH:20])[CH:4]=1)([CH3:1])[CH3:6]

Participants

6

Reactant 3

HCID 8058HexaneHCID 14041698HCID 14041698, compoundHCID 86640072HCID 86640072, compound

Product 1

HCID 178424612HCID 178424612, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8150DiglymeSolvent

Procedure

To a solution of 2a (0.83 g, 5.5 mmol) in anhydrous diethyl ether (5 mL) was added under argon 1.6M methyl lithium in diethyl ether (21 mL, 33.00 mmol) and the mixture was stirred for 3 hrs. at room temperature. After quenching with water, the mixture was extracted with diethyl ether. The extracts were dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to afford a colorless oil (0.86, 95%). A solution of the intermediate product (3-methyl-3-(thiophen-2-yl)butan-2-imine; 0.73 g, 4.36 mmol) and diethyl 2-m-tolylmalonate (0.70 g, 4.36 mmol) in 1 mL diglyme was refluxed at 135° C. for 3 hours. The reaction mixture was cooled and poured into hexane to afford a yellow precipitate, which was collected and crystallized from ethyl acetate/hexane mixture. Off white powder, Yield: 52% MS: (ESI, Neg) 323.90 (M−1) 1HNMR (500 MHz, DMSO-d6): ∂(ppm) 10.69(s, 1H), 10.19(s, 1H), 7.46(d, 1H), 7.11-7.19(m, 3H), 6.99-7.05(m, 3H), 5.78(s, 1H), 2.28(s, 3H), 1.72(s, 6H).

Workup

  1. customat room temperature
  2. customAfter quenching with water
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe extracts were dried over anhydrous Na2SO4
  5. customthe solvent was evaporated under reduced pressure
  6. customto afford a colorless oil (0.86, 95%)
  7. temperatureThe reaction mixture was cooled
  8. customto afford a yellow precipitate, which
  9. customwas collected
  10. customcrystallized from ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-ea071b7130d24db591d49241091e51b6
Source dataset
uspto-grants-2013_01
Patent number
US08349876B2

Reaction notes

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