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tert-Butyl methyl ether → [cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

HRID 858198
Notes
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Reaction equation

HRID 858198 reaction equation
C(O[C@@H:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[O:16][C:17]=2[CH3:18])[CH2:6]1)C=C.I([O-])(=O)(=O)=O.[Na+].[C:32]([O:36]C)(C)(C)[CH3:33]>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:15]2[O:16][C:17]([CH3:18])=[C:13]([CH2:12][O:11][C@@H:7]3[CH2:8][CH2:9][CH2:10][C@H:5]([CH2:33][CH:32]=[O:36])[CH2:6]3)[N:14]=2)=[CH:24][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 23667635Sodium periodateHCID 59659179HCID 59659179, compound

Product 1

HCID 86594504[cis-3-[2-(4-Fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst
HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

2.0 g of 4-(cis-3-allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyl-oxazole are dissolved in 50 ml of diethyl ether, and 3.8 g of sodium periodate, dissolved in 50 ml of water, are added. At 0° C., 1 ml of an osmium tetroxide solution (2.5% by weight in tert-butanol) is added, and the mixture is stirred vigorously at room temperature. After 8 hours, 100 ml of methyl tert-butyl ether are added, and the mixture is washed with a saturated sodium thiosulfate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5). This gives 1.4 g of [cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde as a colorless oil. C20H25NO4 (343.42), MS (ESI): 344 (M+H+), Rf(n-heptane:ethylacetate=1:1)=0.25.

Workup

  1. additionare added
  2. washthe mixture is washed with a saturated sodium thiosulfate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5)

Sources & evidence

ORD record
ord-70d3ad4ceebd425993e1c21a21a030f4
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07148246B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes