Triacetoxyperiodinane → HCID 87870452, compound

HRID 349715Notes

Reaction equation

HRID 349715 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH2:6][O:7][CH2:8][C:9]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][OH:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1)[CH2:6][O:7][CH2:8][C:9]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86602758HCID 86602758, compound

Product 1

HCID 87870452HCID 87870452, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3,5-bis(trifluoromethyl)benzyloxy)-2-methyl-2-phenylpropan-1-ol (500 mg, 1.28 mol) was treated with Dess-Martin periodinane (5.76 g, 15 wt % in CH2Cl2, 2.03 mmol) in methylene chloride for 2 hour at room temperature. The reaction mixture was loaded directly onto silica column and eluted with 5% ethyl acetate in haxanes. 375 mg (75%) of the desired aldehyde was obtained. 1H NMR (500 MHz, CDCl3) δ: 1.60 (s, 3 H) 3.80 (m, 1 H) 4.02 (m, 1 H) 4.62 (m, 2 H) 7.27 (m, 2 H) 7.33 (m, 1 H) 7.39 (m, 2 H) 7.67 (s, 2 H) 7.78 (s, 1 H) 9.61 (s, 1 H).

Workup

  1. washeluted with 5% ethyl acetate in haxanes

Sources & evidence

ORD record
ord-b8f13bb86f594c5da6b3f21bd092473e
Source dataset
uspto-grants-2007_02
Patent number
US07179926B2

Reaction notes

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