Triacetoxyperiodinane → 5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazole-5-carbaldehyde

HRID 1245403Notes

Reaction equation

HRID 1245403 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([SiH2:27][O:28][C:29]([CH3:57])([CH3:56])[C:30]1([CH2:54][OH:55])[O:34][N:33]=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[N:46]=[C:45]([CH3:53])[CH:44]=3)=[CH:37][CH:36]=2)[CH2:31]1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([SiH2:27][O:28][C:29]([CH3:57])([CH3:56])[C:30]1([CH:54]=[O:55])[O:34][N:33]=[C:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]3[C:52]4[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=4)[N:46]=[C:45]([CH3:53])[CH:44]=3)=[CH:37][CH:36]=2)[CH2:31]1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131725995[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]methanol

Product 1

HCID 1317259975-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinate reagent (0.47 g, 1.1 mmol) was added to a solution of the product from step 24b, in methylene chloride (10 mL) under a nitrogen atmosphere at room temperature. The reaction was stirred for 1 h and then partitioned between ethyl acetate and aqueous 10% NaHSO4. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated to give 5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde as a crude oil. MS found: (M+H)+=491.

Workup

  1. custompartitioned between ethyl acetate and aqueous 10% NaHSO4
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-676f584966844b2da3ea2cdc4d82d734
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

Loading…