Tetrahydrofuran → HCID 19380945, compound

HRID 2209450Notes

Reaction equation

HRID 2209450 reaction equation
ClCCCC[C:6]([CH:8]([NH2:11])[CH:9]=C)=O.[CH3:12][Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[CH2:6]=[C:8]([N:11]1[CH2:12][CH2:26][CH2:22][CH2:23][C:24]1=[O:25])[CH3:9]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 19380940HCID 19380940, compound

Product 1

HCID 19380945HCID 19380945, compoundYield 72%

Procedure

To a stirred solution of 26 (2.0 g, 11 mmol) in THF (110 mL) at -78° C. was added NaN(TMS)2 (1.0M in THF, 11 mL) in a stream followed by removal of the cooling bath. After 1.5 hours the reaction mixture was diluted with ethyl acetate and then washed with water, 5% KHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica gel, 60% ethyl acetate/hexanes) gave 27 (1.1 g, 72%) as an oil.

Workup

  1. customfollowed by removal of the cooling bath
  2. additionAfter 1.5 hours the reaction mixture was diluted with ethyl acetate
  3. washwashed with water, 5% KHSO4 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8c6aa76b7fd4a19bd24739eb73e7735
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

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