Trimethylsilyldiazomethane → HCID 71184129, compound

HRID 1519234Notes

Reaction equation

HRID 1519234 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][C:10]=2[C:20]([OH:22])=[O:21])=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:24]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][C:10]=2[C:20]([O:22][CH3:24])=[O:21])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 67458593HCID 67458593, compound

Product 1

HCID 71184129HCID 71184129, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxylic acid (45 mg, 0.132 mmol) in MeOH (2649 μl) was added TMS-diazomethane (132 μl, 0.265 mmol, 2M in Et2O). Additional TMS-diazomethane aliquots were added until no more gas evolution was observed. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica 12 g, 0 to 50% EtOAc in hexane), to give methyl 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxylate (30 mg). methyl 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxylate was reduced using DIBAL, using a similar procedure as described in the preparation of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (INTERMEDIATE B1.1), to provide {5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazol-4-yl}methanol. MS: M+H=326.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica 12 g, 0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-e9c69d5280074fe18f8819a5ce78389d
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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