Formaldehyde → HCID 19756485, compound

HRID 1587770Notes

Reaction equation

HRID 1587770 reaction equation
C(OC(=O)[C:5](=[O:16])[CH:6]([C:14]#[N:15])[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)C.C=O.C([O-])([O-])=O.[Na+].[Na+]>O>[C:14]([CH:6]([C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[CH2:5][OH:16])#[N:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 54250846Ethyl 4-bromo-β-cyano-α-oxobenzenepropanoate

Product 1

HCID 19756485HCID 19756485, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 87 g (0.29 mol) 3-cyano-3-(4-bromophenyl)-2-ketopropionic acid ethyl ester, 44 ml 38% formaldehyde and 180 ml water are added dropwise within 1 hour and with stirring, at a temperature of 10°-15°, a solution of 26 g Na2CO3 in 85 ml water. The mixture is stirred further for 17 hours at room temperature and then three times extracted with 200 ml diethylether. The ether solution is washed with water, dried, evaporated and the residue kept for one hour at 60° under high vacuum. The oily residue (title compound) is chromatographed over a silica gel column with CH2Cl2 /CH3OH 97:3, Rf=0.4.

Workup

  1. additionare added dropwise within 1 hour
  2. stirringThe mixture is stirred further for 17 hours at room temperature
  3. extractionthree times extracted with 200 ml diethylether
  4. washThe ether solution is washed with water
  5. customdried
  6. customevaporated
  7. customThe oily residue (title compound) is chromatographed over a silica gel column with CH2Cl2 /CH3OH 97:3, Rf=0.4

Sources & evidence

ORD record
ord-904b7fb9b2884f25b46bdb5838f4d987
Source dataset
uspto-grants-1993_06
Patent number
US05219876

Reaction notes

Loading…