Acetic Anhydride → HCID 53886620, compound

HRID 2302119Notes

Reaction equation

HRID 2302119 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][OH:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15](OC(=O)C)(=[O:17])[CH3:16]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 15136239HCID 15136239, compound

Product 1

HCID 53886620HCID 53886620, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of 4.13 g (20.7 mmol) 3-hydroxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid tert.-butylester and 244 mg (2 mmol) DMAP in 50 ml pyridine was added 3.06 g (30 mmol) acetic anhydride. The mixture was stirred for 30 min at 0° C., then for additional 60 min at room temperature. The mixture was poured on ice and extracted twice with ether. The combined organic layers were evaporated in vacuo, dissolved in ether, washed with sat. CuSO4, water and brine and dried over MgSO4. Evaporation and bulb-to-bulb distillation gave 4.82 g (97%) 3-acetoxymethyl-2,5-dihydro-pyrrole-1-carboxylic acid tert.-butylester as a colorless oil, b.p. 105° C. (0.2 mbar).

Workup

  1. waitfor additional 60 min at room temperature
  2. additionThe mixture was poured on ice
  3. extractionextracted twice with ether
  4. customThe combined organic layers were evaporated in vacuo
  5. dissolutiondissolved in ether
  6. washwashed with sat. CuSO4, water and brine
  7. dry with materialdried over MgSO4
  8. customEvaporation and bulb-to-bulb distillation

Sources & evidence

ORD record
ord-60cb93e8ad584de7a1d671a254611b5d
Source dataset
uspto-grants-2002_08
Patent number
US06429288B1

Reaction notes

Loading…