Triacetoxyperiodinane → HCID 23072397, compound

HRID 1182507Notes

Reaction equation

HRID 1182507 reaction equation
[OH:1][CH:2]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6]/[C:7](/[CH3:12])=[CH:8]\[C:9]([OH:11])=[O:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.OS([O-])=O.[Na+]>ClCCl.CCOCC>[CH3:12]/[C:7](/[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1)=[O:1])=[CH:8]/[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 23072376HCID 23072376, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23072397HCID 23072397, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 192 (98 mg, 0.33 mmol) in dry dichloromethane (6 mL) was added a solution of Dess-Martin reagent (162 mg, 0.38 mmol) in dry dichloromethane (1 mL) via cannula. The mixture was stirred at room temperature for 24 hours. The mixture was diluted with ether and NaHSO3 (221 mg) in aqueous solution was added with stirring until the phases are homogeneous. The product was extracted, washed with 5% KHSO4, brine, dried over Na2SO4, and finally isolated by chromatography over silica gel (hexanes:Et2O: 4:1 to 1:1) to give 193 in 94% yield. 13CNMR: (75 MHz, CD3OD) δ: 25.2, 25.3, 28.7, 33.7, 39.1, 117.4, 124.7, 127.8, 128.7, 129.0, 129.5, 130.6, 131.0, 137.8, 161.9, 170.1. MS (ESI)=297 (MH+).

Workup

  1. additionwas added
  2. stirringwith stirring until the phases
  3. extractionThe product was extracted
  4. washwashed with 5% KHSO4, brine
  5. dry with materialdried over Na2SO4
  6. customfinally isolated by chromatography over silica gel (hexanes:Et2O: 4:1 to 1:1)

Sources & evidence

ORD record
ord-d74a5e60e757497583f5060d8f071612
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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