Acetic Anhydride → HCID 19774210, compound

HRID 1613645Notes

Reaction equation

HRID 1613645 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH:16]([OH:28])[C:17]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([OH:21])[CH:18]([CH3:20])[CH3:19].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:28][CH:16]([C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[Cl:8])[C:17]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([OH:21])[CH:18]([CH3:19])[CH3:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 19774204HCID 19774204, compound

Product 1

HCID 19774210HCID 19774210, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

38.2 ml (0.4 mol) of acetic anhydride were added dropwise to a solution of 76 g (0.23 mol) of 1-(2,4-dichlorophenyl)-2-(3-pyridyl)-3-methylbutane-1,2-diol, 197.7 ml (1.318 mol) of triethylamine and about 0.5 g (4 mmol) of 4-N,N-dimethylaminopyridine in 1 1 of methylene chloride while heating at 35° C. After cooling to room temperature, the mixture was stirred for a further 30 minutes and then poured into 500 ml of a saturated sodium bicarbonate solution. The organic phase was separated off and was worked up in a conventional manner to obtain the product. The oily crude product was crystallized by stirring with ethyl acetate. Yield: 56%.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was separated off
  3. customto obtain the product
  4. customThe oily crude product was crystallized
  5. stirringby stirring with ethyl acetate

Sources & evidence

ORD record
ord-f906e572af54444786cc53cc5f991250
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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