6-Iodochroman-4-ol → 6-Iodochroman-4-one

HRID 1985051Notes

Reaction equation

HRID 1985051 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH:5]2[OH:12].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12]

Participants

4

Reactant 2

HCID 153258816-Iodochroman-4-olHCID 178418287HCID 178418287, compound

Product 1

HCID 35802626-Iodochroman-4-oneYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (300 ml) suspension of 6-iodo-4-chromanol (15 g, 54.3 mmol) and 30 g of silica gel, at r.t., was added PCC (15.2 g, 70.6 mmol) as a solid. The mixture was stirred at r.t. for 3 h at which time TLC (20% EtOAc/hexanes) indicated complete reaction. The reaction mixture was filtered through a silica gel plug and the filtrate concentrated in vacuo to yield 14.9 g (95%) of 6-iodo-2,3-dihydro-4H-chromen-4-one as a white solid consistent with the literature report (Synthesis 1997, 23-25). HRMS (ESI+) calcd for C9H7IO2 m/z 273.9492; found 273.9500.

Workup

  1. customreaction
  2. filtrationThe reaction mixture was filtered through a silica gel plug
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e978b79a88c44f00a6a48564523ca0c8
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

Loading…