Dichloromethane → HCID 13493680, compound

HRID 2276690Notes

Reaction equation

HRID 2276690 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)O[C:17](=O)[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2)=O.Cl[CH2:29]Cl>>[CH3:29][C:16]1([CH3:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]1[CH:1]=[O:4]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Product 1

HCID 13493680HCID 13493680, compoundYield 85%

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of the product of Example 46d (700 mg, 5.0 mmol) and sodium bicarbonate (420 mg, 5.0 mmol) in dichloromethane (10 mL) at 0° C. under argon was added Dess-Martin periodinane (3.14 g, 7.4 mmol). The reaction mixture was stirred at 0° C. for 2 hours and then slowly warmed to room temperature. The mixture was concentrated under reduced pressure and the residue purified by column silica gel chromatography to give the title compound as a colorless oil (600 mg, Yield: 85% yield). Rf=0.8 (10:1) petroleum ether/:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 9.81 (d, J=2.4 Hz, 1H), 2.10-2.05 (m, 1H), 1.50-1.24 (m, 8H), 1.13 (s, 3H), 0.99 (s, 3H) ppm.

Workup

  1. temperatureslowly warmed to room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue purified by column silica gel chromatography

Sources & evidence

ORD record
ord-5df1c0892d414f3097ca6dc113fbb115
Source dataset
uspto-grants-2015_09
Patent number
US09133082B2

Reaction notes

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