Hydrochloric Acid → 1-(2-Methyl-1H-inden-4-yl)naphthalene

HRID 2298491Notes

Reaction equation

HRID 2298491 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:12][C:11]2[C:6](=[C:7]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]1=O.Cl>C1COCC1.CO>[CH3:3][C:4]1[CH2:12][C:11]2[C:6]([CH:5]=1)=[C:7]([C:13]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=1)[CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22173111HCID 22173111, compound

Product 1

HCID 177791321-(2-Methyl-1H-inden-4-yl)naphthalene

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.3 g (33 mmol) of sodium borohydride were added at 0° C. to a solution of 12 g (44 mmol) of (16) in 100 ml of THF/methanol 2:1 and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured onto 100 g of ice, concentrated hydrochloric acid was added until the pH was 1 and the mixture as extracted a number of times with diethyl ether. The combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The crude product was taken up in 200 ml of toluene, admixed with 0.5 g of p-toluenesulfonic acid and refluxed for 2 hours on a water separator. The reaction mixture was washed 3 times with 509 ml each time of saturated sodium hydrogen carbonate solution and the solvent was removed under reduced pressure. The solid residue was washed with a little pentane and dried under reduced pressure. This gave 10.3 g of (37) in the form of colorless crystals. m.p. 143° C.; 1H-NMR (300 MHz, CDCl3): 7.92-7.18 (10H), 6.11 (m, 1H), 3.42 (s, 2H), 2.07 (3H).

Workup

  1. additionwas added until the pH was 1
  2. extractionthe mixture as extracted a number of times with diethyl ether
  3. washThe combined organic phases were washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. temperaturerefluxed for 2 hours on a water separator
  6. washThe reaction mixture was washed 3 times with 509 ml each time of saturated sodium hydrogen carbonate solution
  7. customthe solvent was removed under reduced pressure
  8. washThe solid residue was washed with a little pentane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-a24166775d0d4dc3ae17bb673e1eb066
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

Loading…