Imidazole → ethyl 8-(iodomethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855056Notes

Reaction equation

HRID 855056 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[CH:23]=[C:24]([CH3:41])[CH:25]=[C:26]2[C:31]=1[O:30][CH:29]([C:32]([F:35])([F:34])[F:33])[C:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:27]2.N1C=CN=C1.[I:47]I>C(Cl)Cl>[I:47][CH2:21][C:22]1[CH:23]=[C:24]([CH3:41])[CH:25]=[C:26]2[C:31]=1[O:30][CH:29]([C:32]([F:35])([F:34])[F:33])[C:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:27]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 69518213ethyl 8-(hydroxymethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517689ethyl 8-(iodomethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The suspension, of polymer bound triphenylphosphine (0.29 g, 0. 88 mmole), in anhydrous CH2Cl2 (5 mL) was cooled to 0° C. (ice bath) and stirred for 15 minutes. The ethyl 8-(hydroxymethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 605b, Step 1 (0.20 g, 0.63 mmole), imidazole (0.06 g, 0.88 mmole) and iodine (0.19 g, 0.76 mmole) were added to above suspension, which was allowed to stir for 15 minutes at 0° C. The mixture was warmed to room temperature and stirred for an additional 3 hours. The resulting mixture was filtered through a plug of celite and condensed in vacuo to give an oil. The oil was purified by flash chromatography (silica gel) with 50% methylene chloride in hexane to give a light yellow oil (0.14 g, 79%): GCMS m/z 426.00 (M+). 1H NMR (CDCl3/400 MHz) 7.64 (s, 1H), 7.11 (s, 1H), 6.94 (s, 1H), 5.79 (q, 1H, J=7.0 Hz), 4.44 (m, 2H), 4.31 (m, 2H), 2.24 (s, 3H), 1.33 (m, 3H).

Workup

  1. additionwere added to above suspension, which
  2. stirringto stir for 15 minutes at 0° C
  3. stirringstirred for an additional 3 hours
  4. filtrationThe resulting mixture was filtered through a plug of celite and condensed in vacuo
  5. customto give an oil
  6. customThe oil was purified by flash chromatography (silica gel) with 50% methylene chloride in hexane

Sources & evidence

ORD record
ord-10efba4a85434e9db3b46b5235e91e11
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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