Tetrahydrofuran → Ethyl (1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)acetate

HRID 2098979Notes

Reaction equation

HRID 2098979 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=O)=[CH:5][CH:4]=1.C[C:15]([CH3:18])([O-:17])C.[K+].C1C[O:23][CH2:22][CH2:21]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:21][C:22]([O:17][CH2:15][CH3:18])=[O:23])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 812767-Methoxy-1,2,3,4-tetrahydronaphthalen-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15720546Ethyl (1,2,3,4-tetrahydro-7-methoxy-1-naphthyl)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 7-methoxy-3,4-dihydronaphthalen-1(2H)-one 46.1 (10.0 g, 56.7 mmol, Aldrich) and triethyl phosphonoacetate (13.6 mL, 68.1 mmol) in THF (250 mL) was added potassium tert-butoxide (1.0M solution in THF (68.1 mL, 68.1 mmol)) via addition funnel over 15 minutes. The resulting mixture was stirred at room temperature for 16 hours (LC-MS showed no difference between 15 minutes and 16 hours) after addition. The mixture was concentrated and re-suspended in hexanes (250 mL). The mixture was passed through a silica gel plug (50 g silica) and rinsed with 1 L of hexanes. The resulting mixture was concentrated to give two pure products (535 mg and 267 mg). Both products were dissolved in EtOH and stirred with Pd/C under H2 for 16 hours. LC-MS showed that both gave the same desired product. The mixture was combined, filtered, and concentrated to give 46.2 (0.77 g, 5.5% yield). MS ESI (pos.) M/E: 249 (M+H).

Workup

  1. additionvia addition funnel over 15 minutes
  2. customno difference between 15 minutes and 16 hours
  3. additionafter addition
  4. concentrationThe mixture was concentrated
  5. washrinsed with 1 L of hexanes
  6. concentrationThe resulting mixture was concentrated
  7. customto give two pure products (535 mg and 267 mg)

Sources & evidence

ORD record
ord-09fca12fba6648c3b3149ef2f3be2e9c
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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