Triacetoxyperiodinane → HCID 25018605, compound

HRID 512001Notes

Reaction equation

HRID 512001 reaction equation
O(CCCCCCC(C1OC(C)=NN=1)=O)C1C=CC=CC=1.[CH2:22]([O:29][C:30]1[CH:50]=[CH:49][C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]([C:43]2[O:44][C:45]([CH3:48])=[N:46][N:47]=2)[OH:42])=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:22]([O:29][C:30]1[CH:50]=[CH:49][C:33]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([C:43]2[O:44][C:45]([CH3:48])=[N:46][N:47]=2)=[O:42])=[CH:32][CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 44128631HCID 44128631, compoundHCID 66931212HCID 66931212, compound

Product 1

HCID 25018605HCID 25018605, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The synthesis was carried out analogous to the preparation of 65.1 using 64.2 (60 mg, 0.15 mmol) and Dess-Martin periodinane (0.127 g, 0.3 mmol) in wet CH2Cl2 (5 mL). Purification by flash column chromatography on silica gel gave pure compound 65.2 (47.5 mg, 80% yield) as a white solid (m p 118-120° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-48e9785deaec44a3bf0bb936366967e3
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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