Pyridine → 5-Phenoxyindan-1-one

HRID 1913410Notes

Reaction equation

HRID 1913410 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]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O: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]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 105852275-Phenoxyindan-1-oneYield 99.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

In an oven-dried round-bottomed flask was combined 5-hydroxy-1-indanone (112 mg, 0.76 mmol), phenylboronic acid (170 mg, 1.51 mmol) and anhydrous copper (II) acetate (195 mg, 1.13 mmol) in 2.5 mL of dichloromethane. Anhydrous pyridine (0.11 mL, 1.5 mmol) was added and the reaction was stirred overnight at room temperature. The reaction was concentrated to dryness and was purified with ISCO column chromatography (Teledyne Isco Inc., Lincoln Nebr.) (0-40% ethyl acetate/heptanes gradient) to give the desired product (SM-1i, 170 mg, 97%) as a clear oil which solidified on standing. MS (ES+) 225.3 (M+H)+. 1H NMR (CDCl3) δ 2.48-2.70 (m, 2H), 2.87-3.08 (m, 2H), 6.78-7.01 (m, 2H), 7.03-7.11 (m, 2H), 7.15-7.30 (m, 1H), 7.32-7.53 (m, 2H), 7.70 (d, 1H).

Workup

  1. customIn an oven-dried round-bottomed flask was combined
  2. concentrationThe reaction was concentrated to dryness
  3. customwas purified with ISCO column chromatography (Teledyne Isco Inc., Lincoln Nebr.) (0-40% ethyl acetate/heptanes gradient)

Sources & evidence

ORD record
ord-96bfbf2c00b541a497f72e77e5fe3c27
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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