Diethyl Ether → HCID 89533759, compound

HRID 920265Notes

Reaction equation

HRID 920265 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC>ClCCl>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:1]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 117638116HCID 117638116, compound

Product 1

HCID 89533759HCID 89533759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 33-4 (0.5 g, 1.884 mmol) in dichloromethane (32 ml) was cooled to 0° C. in an ice bath. Dess-Martin Periodinane (1.199 g, 2.83 mmol) was then added in four portions over 20 minutes. After 1 hour, ether was added and the reaction was quenched with 30 mL of 1N NaOH (aq) followed by vigorous stirring for 30 minutes. The layers were then separated. The organic layer was dried over Sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane) to yield 33-5.

Workup

  1. customthe reaction was quenched with 30 mL of 1N NaOH (aq)
  2. customThe layers were then separated
  3. dry with materialThe organic layer was dried over Sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel column chromatography (0-30% EtOAc in hexane)
  7. customto yield 33-5

Sources & evidence

ORD record
ord-ccd28a39933043a4bacaf6e1ca80f95e
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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