Trifluoroacetic acid → 4-Methoxy-5-methyl-2-(4-nitro-phenoxy)-indan

HRID 389322Notes

Reaction equation

HRID 389322 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[C:7]2=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:7]2

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 668130954-Methoxy-5-methyl-2-(4-nitro-phenoxy)-indan-1-one

Product 1

HCID 668129614-Methoxy-5-methyl-2-(4-nitro-phenoxy)-indanYield 70.3%

Conditions

Temperature
62.5 °C

Procedure

To a mixture of 4-Methoxy-5-methyl-2-(4-nitro-phenoxy)-indan-1-one (1.8 gm, 0.0057 mole) and Triethyl silane (9.0 ml, 0.0564 mole), Trifluoroacetic acid (18 ml) was added at 20-25° C. The reaction mixture was heated to 60-65° C. for 3 hours and then poured into saturated Sodium bicarbonate solution. It was extracted with Ethylacetate (2×100 ml), dried over Sodium sulphate, distilled under vacuum to give a crude product which was purified by column chromatography using Ethyl acetate:Hexane (2:98) as a mobile phase. The collected fractions were distilled under vacuum to give 1.2 gm of desired product as a solid.

Workup

  1. additionwas added at 20-25° C
  2. extractionIt was extracted with Ethylacetate (2×100 ml)
  3. dry with materialdried over Sodium sulphate
  4. distillationdistilled under vacuum
  5. customto give a crude product which
  6. customwas purified by column chromatography
  7. distillationThe collected fractions were distilled under vacuum

Sources & evidence

ORD record
ord-a1942ddd212540a99e85a7c133b86da6
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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