Tetrahydrofuran → HCID 18352635, compound

HRID 429757Notes

Reaction equation

HRID 429757 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[S:12]1[CH:16]=[C:15]([CH2:17][CH:18]([C:20]([OH:22])=[O:21])[NH2:19])[N:14]=[CH:13]1.C1COCC1.[C:28]1([C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N+]=[N-])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[C:28]1([CH:34]([O:21][C:20](=[O:22])[CH:18]([CH2:17][C:15]2[N:14]=[CH:13][S:12][CH:16]=2)[NH2:19])[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 18352641HCID 18352641, compound

Product 1

HCID 18352635HCID 18352635, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After 21.84 g (123.6 mmol) of the compound (48) was dissolved in ethanol (200 ml) and THF (100 ml) with heating to the solution was added diphenyldiazomethane (24 g, 123.6 mmol) under ice-cooling over 35 min. little by little. The cooling bath was removed and the mixture was stirred for 1 h at room temperature. To the reaction mixture was added acetic acid (0.1 ml) for quenching the excess reagent, and the mixture was concentrated in vacuo. The residue was crystallized from ether and ethanol to yield 31.63 g (97.7%) of the compound (49).

Workup

  1. temperaturecooling over 35 min. little by little
  2. customThe cooling bath was removed
  3. additionTo the reaction mixture was added acetic acid (0.1 ml)
  4. customfor quenching the excess reagent
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe residue was crystallized from ether and ethanol

Sources & evidence

ORD record
ord-7429e4e92e924d94882da908493964fa
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

Loading…