Chloroform → HCID 21298941, compound

HRID 34718Notes

Reaction equation

HRID 34718 reaction equation
[CH3:1][CH:2]1[CH2:7][C@H:6]([OH:8])[C@@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[O:12]=[C:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)/[CH:14]=[CH:15]/[C:16](O)=[O:17].C(Cl)(Cl)Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH:2]1([CH3:1])[CH2:3][CH2:4][CH:5]([CH:9]([CH3:11])[CH3:10])[CH:6]([O:8][C:16](=[O:17])/[CH:15]=[CH:14]/[C:13](=[O:12])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 676116Benzoylacrylic acidHCID 12285346HCID 12285346, compound

Product 1

HCID 21298941HCID 21298941, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4.43 g (0.028 mole) of (+)-menthol and 0.34 g (0.003 mole) of 4-dimethylaminopyridine are added to a solution of 5.0 g (0.028 mole) of (E)-4-oxo-4-phenyl-2-butenoic acid in 60 ml of anhydrous dichloromethane. After cooling the solution to 0° C., a solution of 5.86 g (0.028 mole) of N,N-dicyclohexylcarbodiimide in 20 ml of anhydrous dichloromethane is added. The mixture is stirred at 0° C. for 30 minutes, then at room temperature for one hour. The reaction mixture is worked up as described in Example 1 to give the crude product as a dark-brown oil in a yield of 8.1 g (91%) which is purified by using column chromatography as described in Example 1. The named compound is obtained in a yield of 6.7 g, Rf =0.78 (dichloromethane); [α]D25 =+65° (c=2.0, chloroform).

Workup

  1. waitat room temperature for one hour
  2. customto give the crude product as a dark-brown oil in a yield of 8.1 g (91%) which
  3. customis purified
  4. customThe named compound is obtained in a yield of 6.7 g, Rf =0.78 (dichloromethane)

Sources & evidence

ORD record
ord-9b80dda00d724f75ba8130db29d4c26d
Source dataset
uspto-grants-1988_08
Patent number
US04762944

Reaction notes

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