Toluene → HCID 16110495, compound

HRID 2177387Notes

Reaction equation

HRID 2177387 reaction equation
[H-].[Na+].C1(C)C=CC=CC=1.C(OP([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(OCC)=O)C.[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[C:31](=O)[CH2:30][CH2:29]2>O>[CH3:24][O:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)/[C:31](=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])/[CH2:30][CH2:29]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 787875-Methoxyindan-1-one

Product 1

HCID 16110495HCID 16110495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed sodium hydride (1 g, 46.00 mmol, 2.50 equiv), toluene (150 mL), ethyl 2-(diethoxyphosphoryl)acetate (7 g, 31.22 mmol, 1.69 equiv). This was followed by the addition of 5-methoxy-2,3-dihydro-1H-inden-1-one (3 g, 18.50 mmol, 1.00 equiv) at 30° C. The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting solution was diluted with 10 mL of water. The resulting solution was extracted with 3×100 mL of toluene and the organic layers combined. The resulting mixture was washed with 2×20 mL of sodium chloride. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (30:70). This resulted in 2 g (47%) of ethyl 2-[(1E)-5-methoxy-2,3-dihydro-1H-inden-1-ylidene]acetate as yellow oil.

Workup

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe resulting solution was extracted with 3×100 mL of toluene
  4. washThe resulting mixture was washed with 2×20 mL of sodium chloride
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 2 g (47%) of ethyl 2-[(1E)-5-methoxy-2,3-dihydro-1H-inden-1-ylidene]acetate as yellow oil

Sources & evidence

ORD record
ord-6e3518a92e574a00a770ac43d2fd301d
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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