Acetic Anhydride → HCID 22755584, compound

HRID 1742418Notes

Reaction equation

HRID 1742418 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(Cl)Cl>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][C:12](=[O:14])[CH3:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 22755584HCID 22755584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hydroxy-indan-1-one (1600 mg, 10.8 mmol)in CH2Cl2 (20 mL) at 23° C. were added 4-N,N-dimethylaminopyridine (1830 mg, 15 mmol) and acetic anhydride (1500 mg, 1.4 mL, 15 mmol). The reaction mixture was stirred for 25 hours, quenched with 10% hydrochloric acid (HCl) (20 mL) and diluted with CHCl3 (500 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 (20 mL), dried (MgSO4)and concentrated in vacuo. 1H NMR (250 MHz, CDCl3): d 7.78 (d, 2 H), 7.21 (s, 1 H), 7.10 (d, 1 H), 3.28 (t, 2 H), 2.75 (t, 2 H), 2.38 (s, 3 H).

Workup

  1. customquenched with 10% hydrochloric acid (HCl) (20 mL)
  2. additiondiluted with CHCl3 (500 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NaHCO3 (20 mL), dried (MgSO4)and
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccc6c823affb4316b18a9da832488e97
Source dataset
uspto-grants-1994_08
Patent number
US05338740

Reaction notes

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