Diethyl Ether → HCID 86756237, compound

HRID 566505Notes

Reaction equation

HRID 566505 reaction equation
[C:1]([O:5][P:6]([C:13]([F:43])([F:42])[C:14]1[CH:41]=[CH:40][C:17]([CH2:18][CH:19]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:16][CH:15]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:46][C:47]([F:57])([F:56])[C:48]1[CH:55]=[CH:54][C:51]([CH2:52]Br)=[CH:50][CH:49]=1.CCOCC>CN(C=O)C>[C:9]([O:8][P:6]([C:13]([F:43])([F:42])[C:14]1[CH:41]=[CH:40][C:17]([CH2:18][C:19]([CH2:52][C:51]2[CH:50]=[CH:49][C:48]([C:47]([F:46])([F:56])[F:57])=[CH:55][CH:54]=2)([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:16][CH:15]=1)([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86756238HCID 86756238, compound

Product 1

HCID 86756237HCID 86756237, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Example 18, Step 1 (94 mg, 0.15 mmol) in DMF (2 mL) at 0° C. was added NaH (5.5 mg, 80% in oil). After 15 min., 4-(trifluoromethyl)benzyl bromide (44 mg, 0.18 mmol) was added. After 2 h at 0° C., the mixture was given a standard aqueous/Et2O work-up, and the residue was purified by flash chromatography (1:10 EtOAc/hexane) to give a syrup (53 mg).

Workup

  1. waitAfter 2 h at 0° C.
  2. customthe residue was purified by flash chromatography (1:10 EtOAc/hexane)

Sources & evidence

ORD record
ord-5bd58af83f1146da8a3213ff5c0d2318
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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