Dimethylformamide dimethyl acetal → HCID 15029614, compound

HRID 893083Notes

Reaction equation

HRID 893083 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[CH:13](O)[C@@H:14](C(O)=O)[NH:15][CH:16]=[O:17].COC(OC)N(C)C>C(Cl)(Cl)Cl>[CH:16]([NH:15]/[CH:14]=[CH:13]/[C:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])=[O:17]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 53759826HCID 53759826, compound

Product 1

HCID 15029614HCID 15029614, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-methoxy-5, 6, 7, 8-tetrahydronaphth-1-yl)-N-formylserine (2930 mg, 10 mmol) and N,N-dimethylformamide dimethyl acetal (7100 mg, 60 mmol) in dry chloroform (50 ml) is heated at reflux temperature for 2 hrs. The reaction mixture is evaporated under vacuum, the residue dissolved in chloroform and filtered through a silica gel column. The eluateis evaporated under vacuum to give almost pure title compound in 85% yield (1970 mg).

Workup

  1. temperatureat reflux temperature for 2 hrs
  2. customThe reaction mixture is evaporated under vacuum
  3. dissolutionthe residue dissolved in chloroform
  4. filtrationfiltered through a silica gel column
  5. customThe eluateis evaporated under vacuum

Sources & evidence

ORD record
ord-2287fadbd056492e95c91ab671cf7295
Source dataset
uspto-grants-1992_06
Patent number
US05122537

Reaction notes

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