Phenol → 1-Indanone

HRID 735290Notes

Reaction equation

HRID 735290 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N([CH2:13][CH3:14])CC)C.Cl[C:16](OC)=[O:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]1(=[O:17])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 996PhenolHCID 6586Methyl chloroformateHCID 8471Triethylamine

Product 1

HCID 67351-IndanoneYield 99%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (2 mL) solution of the phenol from Example 31 (10.5 mg, 0.03 mmol) was added triethylamine (21 μL, 5 eq), DMAP (0.5 M dichloromethane solution, 6 μL, 0.1 eq) and methyl chloroformate (4.6 μL, 2 eq). The mixture was stirred at room temperature for 1.5 h, concentrated and purified by reverse-phase HPLC (70 to 100% solvent B) to give Example 32 (12 mg, 99%). MS Found: (M+H)+=409.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse-phase HPLC (70 to 100% solvent B)

Sources & evidence

ORD record
ord-43d2708db14b4639b7d62d64868cd000
Source dataset
uspto-grants-2009_09
Patent number
US07592461B2

Reaction notes

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