Ammonium Chloride → HCID 18349870, compound

HRID 1648686Notes

Reaction equation

HRID 1648686 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:15])([CH3:14])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]=2[CH:5]=1)(=O)[CH3:2].C(OP([CH2:26][C:27]([O:29][CH3:30])=[O:28])(OCC)=O)C.[CH3:31][O-].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:14][C:10]1([CH3:15])[CH2:9][CH2:8][C:7]([CH3:17])([CH3:16])[C:6]2[CH:5]=[C:4](/[C:1](/[CH3:2])=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:13]=[CH:12][C:11]1=2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 66113Methyl diethylphosphonoacetateHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 18349870HCID 18349870, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-acetyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene (33, 4.60 g, 20.0 mmol) and methyl diethylphosphonoacetate (7.33 g, 34.9 mmol) in anhydrous toluene (80 mL) was treated dropwise via syringe with sodium methoxide (25 wt % in methanol, 5.5 mL, 24.0 mmol) at room temperature under argon. The reaction mixture was stirred for 14 h and then poured into a separatory funnel containing diethyl ether and saturated ammonium chloride solution. The layers were agitated and separated, and the organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 6.5 g of a pale yellow oil. Purification by column chromatography (20:1 ratio silica gel/crude product; elution with 10% ethyl acetate/hexanes) gave 4.10 g (72%) of 34 as a clear, colorless oil. 1H NMR (300 MHz, CDCl3) δ7.40 (d, J=2 Hz, 1H, ArH), 7.30 (d, J=7 Hz, 1H, ArH), 7.25 (dd, J=2, 8 Hz, 1H, ArH), 6.15 (br s, 1H, C=CH), 3.75 (s, 3H, CO2CH3), 2.58 (s, 3H, CH3C=C), 1.67 (s, 4H, CH2CH2), 1.26 (s, 6H, 2×CH3), and 1.28 (s, 6H, 2×CH3).

Workup

  1. additionpoured into a separatory funnel
  2. stirringThe layers were agitated
  3. customseparated
  4. washthe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc073cbd3b75480497b4436e860c6c51
Source dataset
uspto-grants-1995_07
Patent number
US05436369

Reaction notes

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