Ethyl formate → HCID 15718671, compound

HRID 2165370Notes

Reaction equation

HRID 2165370 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[C:12]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:31](OCC)=[O:32]>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[CH:14][C:13]=3[C:12]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[C:11]2[CH:31]=[O:32])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 15718670HCID 15718670, compoundHCID 178418339Butyllithium

Product 1

HCID 15718671HCID 15718671, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35.2mg (0.lmM) of the product of Step 4, above, in 4ml of absolute THF is cooled to -40° to -50°. To this is then slowly added 0.075ml (0.12mM) of n-butyllithium (1.6M in hexane) and the mixture stirred for 1 hour at -40° to -50°. 0.1 ml (1.2mM) of ethyl formate is added with stirring for 2 hours at -40° to -50°. The mixture is quenched with aqueous ammonium chloride and extracted with ethyl acetate. The resulting solution is dried over Na2SO4 and evaporated to dryness. The resulting product is applied to prep plates in CH2Cl2 /CH3OH (98:2) and the bands eluted with ethyl acetate to give the title product of this step as a yellow gum.

Workup

  1. customThe mixture is quenched with aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe resulting solution is dried over Na2SO4
  4. customevaporated to dryness
  5. washthe bands eluted with ethyl acetate

Sources & evidence

ORD record
ord-43c327a31d0946e2879ea84042b88f0d
Source dataset
uspto-grants-1990_07
Patent number
US04939159

Reaction notes

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