Thiophenol → ethyl 6-methyl-8-[(phenylthio)methyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855055Notes

Reaction equation

HRID 855055 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.[C:42]1([SH:48])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:41][C:24]1[CH:25]=[C:26]2[C:31](=[C:22]([CH2:21][S:48][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH:23]=1)[O:30][CH:29]([C:32]([F:34])([F:35])[F:33])[C:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:27]2

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69518213ethyl 8-(hydroxymethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69519570ethyl 6-methyl-8-[(phenylthio)methyl]-2-(trifluoromethyl)-2H-chromene-3-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The polymer bound triphenylphosphine (1.2 g, 3.6 mmole) was suspended in anhydrous THF (10 mL) and the mixture was allowed to stir for 15 minutes. The ethyl 8-(hydroxymethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 605b, Step 1 (0.38 g, 1.20 mmole), benzenethiol (0.20 g, 1.80 mmole) and DEAD (0.31 g, 1.80 mmole) were added to above mixture, which was allowed to stir for 18 hours. The resulting mixture was filtered through a plug of celite and condensed in vacuo to give a yellow oil (0.49 g, 98%). No further purification was performed. GCMS m/z 408.0 (M+).

Workup

  1. additionwere added to above mixture, which
  2. stirringto stir for 18 hours
  3. filtrationThe resulting mixture was filtered through a plug of celite and condensed in vacuo

Sources & evidence

ORD record
ord-23472c31f07f4ea1bd5a897d57c6cd8a
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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