Diethyl Ether → HCID 57283505, compound

HRID 1454293Notes

Reaction equation

HRID 1454293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:29](N1CCOCC1)=[O:30].C(OCC)C>O1CCCC1>[CH:29]([C:11]1[O:12][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:9]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:10]=1)=[O:30]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 20417N-FormylmorpholineHCID 2733832Lithium HexamethyldisilazideHCID 53850091HCID 53850091, compound

Product 1

HCID 57283505HCID 57283505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 4-[5-(4-fluoro-phenyl)-oxazol-4-yl]-pyridine (1.5 g, Reference Example 6) in dry tetrahydrofuran (50 ml), under an inert atmosphere and at −10° C., was treated with a solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (12.5 ml, 1M). After 0.5 hour the mixture was treated with N-formylmorpholine (1.5 ml). This mixture was stirred at room temperature for 16 hours then treated with diethyl ether (50 ml) and then filtered. The solid was suspended in 10% aqueous ammonium chloride solution (50 ml) and the resulting yellow solid filtered to give the title compound. MS: 269 [MH+].

Workup

  1. filtrationfiltered
  2. filtrationthe resulting yellow solid filtered

Sources & evidence

ORD record
ord-8096d6c6e27646998f5d278e5875fa46
Source dataset
uspto-grants-2009_01
Patent number
US07479501B2

Reaction notes

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