Acetic Anhydride → HCID 21538621, compound

HRID 1076886Notes

Reaction equation

HRID 1076886 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][C:14]3([C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]([OH:25])[CH2:17]3)[CH2:13]2)=[CH:4][CH:3]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28].[OH-].[Na+]>N1C=CC=CC=1>[C:27]([O:25][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]2([CH2:15][CH2:16][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:26])[CH2:13]2)[CH2:17]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 54334119HCID 54334119, compound

Product 1

HCID 21538621HCID 21538621, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.5 g of p-fluoro-4-(3-hydroxyspiro[indan-1,3'-pyrrolidin]-1'-yl)butyrophenone are stirred at room temperature with 15 cc of pyridine and 15 cc of acetic anhydride for 18 hours. The mixture is then poured on ice, is rendered alkaline with 2 N caustic soda solution and is extracted thrice with 50 cc of ether. The ether phase is washed with water, dried over sodium sulphate and concentrated by evaporation. The oily residue is converted into the hydrogen furmarate, which is recrystallized from ethanol/ether. The hydrogen fumarate of the title compound has a M.P. of 154°-156°.

Workup

  1. additionThe mixture is then poured on ice
  2. extractionis extracted thrice with 50 cc of ether
  3. washThe ether phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customis recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-f74c37386afc4d63a998c91154b2229e
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

Loading…