Triacetoxyperiodinane → HCID 87279590, compound

HRID 2040270Notes

Reaction equation

HRID 2040270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][C:9]=2[CH2:16][OH:17])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][C:11]([F:15])([F:14])[CH2:10][C:9]=2[CH:16]=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67126888HCID 67126888, compound

Product 1

HCID 87279590HCID 87279590, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 321D (1.38 g) in dichloromethane (25 mL) was added Dess-Martin periodinane (2.489 g) and the reaction stirred for 1 hour at room temperature. The reaction was quenched with 1N aqueous NaOH solution (75 mL) and the product was extracted into dichloromethane (2×100 mL). The combined organics were washed with brine (75 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 80 g) eluting with a gradient of 1% to 10% ethyl acetate/hexanes over 40 minutes gave the title compound.

Workup

  1. customThe reaction was quenched with 1N aqueous NaOH solution (75 mL)
  2. extractionthe product was extracted into dichloromethane (2×100 mL)
  3. washThe combined organics were washed with brine (75 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Reveleris 80 g) eluting with a gradient of 1% to 10% ethyl acetate/hexanes over 40 minutes

Sources & evidence

ORD record
ord-ad794c5955454fda9b56423d8a1d5941
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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