Ethyl formate → HCID 19002304, compound

HRID 2260009Notes

Reaction equation

HRID 2260009 reaction equation
[C:1]([P:5]([C:11]([F:20])([F:19])[C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[CH:26](OCC)=[O:27].[NH4+].[Cl-]>CCOCC>[C:1]([P:5]([C:11]([F:20])([F:19])[C:12]1[CH:17]=[CH:16][C:15]([CH:26]=[O:27])=[CH:14][CH:13]=1)([C:7]([CH3:10])([CH3:9])[CH3:8])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 25517Ammonium ChlorideHCID 19002293HCID 19002293, compound2×HCID 178418339Butyllithium

Product 1

HCID 19002304HCID 19002304, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

To compound 27 (50 mg, 0.12 mmol ) in anhydrous ether (0.63 mL) at -78° C. under argon was added n-BuLi (1.6M in hexanes, 0.12 mL, 0.19 mmol) and the mixture was stirred at -78° C. (20 minutes). A solution of ethyl formate, 1M in ether (0.25 mmol, 2 eq.) was added and the mixture stirred (0.5 hours at -78° C.). Saturated aqueous NH4Cl (1 mL) was added and the mixture warmed to ambient temperature and extracted with ether (3×1 mL). The combined extracts were dried (MgSO4) and taken to dryness under reduced pressure, affording 43 mg of crude 28, however, contaminated with starting material 27.

Workup

  1. stirringthe mixture stirred (0.5 hours at -78° C.)
  2. temperaturethe mixture warmed to ambient temperature
  3. extractionextracted with ether (3×1 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customaffording 43 mg of crude 28

Sources & evidence

ORD record
ord-b2ad3d6000ae4755be7bd5ea5936a4b7
Source dataset
uspto-grants-1995_12
Patent number
US05475129

Reaction notes

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