Triacetoxyperiodinane → (R)-Methyl 5-(3-(3-formyl-1,1-dioxidoisothiazolidin-2-yl)propyl)thio-phene-2-carboxylate

HRID 524364Notes

Reaction equation

HRID 524364 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH2:24][C@H:25]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[N:26]1[CH2:32][CH2:33][CH2:34][C:35]1[S:39][C:38]([C:40]([O:42][CH3:43])=[O:41])=[CH:37][CH:36]=1>C(Cl)Cl>[CH:24]([C@H:25]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[N:26]1[CH2:32][CH2:33][CH2:34][C:35]1[S:39][C:38]([C:40]([O:42][CH3:43])=[O:41])=[CH:37][CH:36]=1)=[O:23]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 118688790(R)-Methyl 5-(3-(3-(hydroxymethyl)-1,1-dioxidoisothiazolidin-2-yl)-propyl)-thiophene-2-carboxylate

Product 1

HCID 118688787(R)-Methyl 5-(3-(3-formyl-1,1-dioxidoisothiazolidin-2-yl)propyl)thio-phene-2-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (476 mg, 1.00 mmol) was added to a solution of the alcohol 10 (312 mg, 0.94 mmol) in CH2Cl2 (3.0 mL) at 23° C. The reaction was stirred for 16 h, filtered through celite and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 10% EtOAc/hex) afforded 155 mg (50%) of aldehyde 11.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel, 10% EtOAc/hex)

Sources & evidence

ORD record
ord-d1f70f9b52bd410abe201c7b0aff4205
Source dataset
uspto-grants-2016_05
Patent number
US09340534B2

Reaction notes

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