Water → 2-[[(5,6,7,8-Tetrahydro-8-methylene-2-naphthalenyl)oxy]methyl]quinoline

HRID 543295Notes

Reaction equation

HRID 543295 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CCCCCC.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([CH2:28]CCC2=O)=[CH:26][CH:25]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCOCC>[CH2:4]=[C:3]1[C:26]2[CH:25]=[C:24]([O:23][CH2:22][C:13]3[CH:14]=[CH:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]=3)[CH:33]=[CH:32][C:27]=2[CH2:28][CH2:1][CH2:2]1

Participants

8

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 138511063,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenoneHCID 178418339Butyllithium

Product 1

HCID 138511142-[[(5,6,7,8-Tetrahydro-8-methylene-2-naphthalenyl)oxy]methyl]quinolineYield 24%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3.6 g (10.1 mmol) of methyltriphenylphosphonium bromide in 50 mL tetrahydrofuran under nitrogen at -50° C. is added n-butyllithium (10 mm as a hexane solution (2.1 M)). After 45 minutes, a solution of 3.0 g (9.90 mmol) of 3,4-dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone, prepared according to Example 1A above, in 50 mL tetrahydrofuran is added dropwise and the reaction mixture is allowed to slowly come to room temperature. After three days, 50 mL water and 50 mL ether is added. The organic layer is separated, dried over magnesium sulfate and evaporated to 5.0 g of crude product. Chromatography accords 1.3 g (44%) of the desired product. Recrystallization from hexane gives 0.70 g (24%) of white crystals mp 56°-58° C.

Workup

  1. additionis added dropwise
  2. customto slowly come to room temperature
  3. waitAfter three days
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to 5.0 g of crude product
  7. customRecrystallization from hexane

Sources & evidence

ORD record
ord-468c6a5cd7d6434a87dd3132617aee8c
Source dataset
uspto-grants-1987_04
Patent number
US04661596

Reaction notes

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