Water → 8-methoxy-9-[2-(thiophene-2-yl)vinyl]-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine

HRID 85266Notes

Reaction equation

HRID 85266 reaction equation
C1([Li])C=CC=CC=1.[Cl-].[C:9]1([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:13][CH:12]=[CH:11][CH:10]=1.[CH3:34][O:35][C:36]1[C:47]2=[C:48]3[N:43]([CH2:44][CH2:45][CH2:46]2)[CH2:42][CH2:41][CH2:40][C:39]3=[CH:38][C:37]=1[CH:49]=O.O>O1CCCC1.C(OCC)(=O)C>[CH3:34][O:35][C:36]1[C:47]2=[C:48]3[N:43]([CH2:44][CH2:45][CH2:46]2)[CH2:42][CH2:41][CH2:40][C:39]3=[CH:38][C:37]=1[CH:49]=[CH:14][C:9]1[S:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8202598-methoxy-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoline-9-carbaldehydeHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 178506676HCID 178506676, compound

Product 1

HCID 680093408-methoxy-9-[2-(thiophene-2-yl)vinyl]-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizineYield 63.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 30 ml of tetrahydrofuran was added 3.2 g of phenyllithium (19% solution in dibutylether) (7.23 mmol), and 2.6 g (6.58 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling. Next, 1.5 g (6.49 mmol) of 8-methoxy-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinolizine-9-carboaldehyde was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred for 1.5 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 1.29 g of an orange oily matter (yield: 63.9%).

Workup

  1. additionwas added
  2. additionadded dropwise
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. customThe residue was purified by silica gel column chromatography
  6. customto give 1.29 g of an orange oily matter (yield: 63.9%)

Sources & evidence

ORD record
ord-9c4f389b79294eacb529b3abd4a4face
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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