Triacetoxyperiodinane → (R)-3-(Benzyloxy)-2-(4-bromo-2-methylphenyl)propanal

HRID 708861Notes

Reaction equation

HRID 708861 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[CH3:20])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:8][CH2:9][C@@H:10]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[CH3:20])[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118092700HCID 118092700, compound

Product 1

HCID 118092989(R)-3-(Benzyloxy)-2-(4-bromo-2-methylphenyl)propanalYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 16F (2.83 g, 8.44 mmol) in dichloromethane (60 ml) was added Dess-Martin periodinane (4.30 g, 10.13 mmol) at rt. The reaction was stirred at rt for 2 h. The mixture was filtered and the filtrate was concentrated. The crude product was purified by flash chromatography (0-30% ethyl acetate/hexanes). The desired fractions were combined, concentrated to give 16G (2.0 g, 6.00 mmol, 71.1% yield) as colorless oil. MS (ESI) (m/z): 331.3, 333.3 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ ppm 9.72 (s, 1H) 7.40 (d, J=1.77 Hz, 1H) 7.24-7.38 (m, 6H) 6.95 (d, J=8.08 Hz, 1H) 4.46-4.61 (m, 2H) 4.02-4.16 (m, 2H) 3.67-3.81 (m, 1H) 2.34 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by flash chromatography (0-30% ethyl acetate/hexanes)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-41c720175b8542cbbfabf4aed5c1cce1
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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