Acetic Anhydride → HCID 56986525, compound

HRID 439859Notes

Reaction equation

HRID 439859 reaction equation
[CH3:1][C:2]12[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10]1([CH3:18])[C:9]1[CH:8]=[C:7]([CH3:19])[CH:6]=[CH:5][C:4]=1[NH:3]2.C(=O)(O)[O-].[Na+].[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:3]1[C:4]2[CH:5]=[CH:6][C:7]([CH3:19])=[CH:8][C:9]=2[C@@:10]2([CH3:18])[CH2:11][C:12]3[C:17]([C@@:2]12[CH3:1])=[CH:16][CH:15]=[CH:14][CH:13]=3)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 22408461HCID 22408461, compound

Product 1

HCID 56986525HCID 56986525, compound

Procedure

4b,5,9b,10-Tetrahydro-4b,8,9b-trimethylindeno[1,2-b]indole (0.25 g, 1.00 mmol) was dissolved in acetic anhydride (1 cm3) and stirred at room temperature for 16 hours. The reaction mixture was poured into saturated sodium bicarbonate solution (25 cm3) and stirred for 1/2 hour. The mixture was extracted with diethyl ether (3×10 cm3) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography on silica gel eluting with 4% ethyl acetate/60°-80° petrol to yield a pale yellow gum. Yield: 0.15 g, 53%. 1H NMR (CDCl3) δ: 7.84 (1H, s), 6.90-7.23 (6H, m), 3.26 (1H, d, J=15.9 Hz), 2.96 (1H, d, J =15.9 Hz), 2.40 (3H, s), 2.31 (3H, s), 1.77 (3H, s), 1.32 (3H, s).

Workup

  1. stirringstirred for 1/2 hour
  2. extractionThe mixture was extracted with diethyl ether (3×10 cm3)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude material was purified by flash chromatography on silica gel eluting with 4% ethyl acetate/60°-80° petrol
  7. customto yield a pale yellow gum

Sources & evidence

ORD record
ord-3f3167c3a0034b46af92585ba1b5a2b5
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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