Dimethylformamide → HCID 18936591, compound

HRID 2294990Notes

Reaction equation

HRID 2294990 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13](CO)[O:12][C:11](=[O:16])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22]Br.CN([CH:36]=[O:37])C>CCCCCC.CCOC(C)=O>[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH2:22][O:37][CH2:36][CH:10]2[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:13][O:12][C:11]2=[O:16])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 53720210HCID 53720210, compound

Product 1

HCID 18936591HCID 18936591, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

Treat a solution of 4-(3,4-dichlorophenyl)-dihydro-5-(hydroxymethyl) 2(3H)-furanone (3.3 g, 12.6 mmol, 3:2 ratio of stereoisomers by NMR) in dry DMF(10 mL) with 3,5-bistrifluoromethylbenzyl bromide (5.9 mL, 32.2 mmol) followed by Ag2O (5.8 g, 25.3 mmol); wrap the vessel in foil and stir for 2.5 d. Apply the crude material to a pad of silica gel (10 cm×4 cm) packed with hexane:EtOAc (1:1), washing the pad with the same solvent until no further product is eluted as shown by TLC; concentrate the resulting filtrate in vacuo to give the crude product as a solid (10 g). Dissolve the crude was dissolved in hexane:EtOAc (4:1) and purify by silica gel chromatography (column: 7.5×19; solvent: hexane:EtOAc, 4:1) to give 3.33 g (6.8 mmol, 54%) of isomer (trans)-[[[(3,5-bis(trifluoromethyl)phenyl]methoxy]methyl]-4-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 1.08 g (2.2 mmol, 17%) of the corresponding cis isomer for a total yield of 71%.

Workup

  1. washwashing the pad with the same solvent until no further product
  2. washis eluted
  3. concentrationconcentrate the resulting filtrate in vacuo
  4. customto give the crude product as a solid (10 g)
  5. dissolutionDissolve the crude
  6. custompurify by silica gel chromatography (column: 7.5×19; solvent: hexane:EtOAc, 4:1)

Sources & evidence

ORD record
ord-255ea57eef364bfaae4ec6fe52eb3360
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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