Triacetoxyperiodinane → [6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetaldehyde

HRID 713983Notes

Reaction equation

HRID 713983 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][CH2:23][OH:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][CH:23]=[O:24])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 669266452-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol

Product 1

HCID 86668430[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-acetaldehydeYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanol (170 mg, 0.52 mmol) in methylene chloride (5 mL) was added Dess-Martin periodinane (0.31 g, 0.73 mmol). After stirred at room temperature for 1 hour, the solution was diluted with methylene chloride, washed with sodium thiosulfate aqueous, dried over Na2SO4, and concentrated. The crude was purified via silica gel column to afford white solid (120 mg, yield: 70%). ESI-MS: 325.20 (M+H)+.

Workup

  1. washwashed with sodium thiosulfate aqueous
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude was purified via silica gel column

Sources & evidence

ORD record
ord-f3075bd42dc5431f8fb5045f7e438c2a
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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