Sodium hydride → HCID 59659237, compound

HRID 253360Notes

Reaction equation

HRID 253360 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][C:9]1[O:13][C:12]([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[N:11][C:10]=1[CH2:21][O:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31](=[CH2:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:24]1>CS(C)=O>[CH3:8][C:9]1[O:13][C:12]([C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[N:11][C:10]=1[CH2:21][O:22][C@H:23]1[CH2:28][CH2:27][CH2:26][C@@H:25]([O:29][CH2:30][C:31]2([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:4][CH2:37]2)[CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 59659186HCID 59659186, compound

Product 1

HCID 59659237HCID 59659237, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

At room temperature, 12 mg of a 60 percent strength sodium hydride suspension are added to a suspension of 55 mg of trimethylsulfonium iodide in 2 ml of DMSO, and the mixture is stirred at room temperature for 20 min. At 10° C., 100 mg of ethyl (1R,3S)-2-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]acrylate, dissolved in 2 ml of DMSO, are then added, and the mixture is stirred at room temperature for 90 min. The mixture is poured into ice-water and extracted with methyl tert-butyl ether. The organic phase is dried over sodium sulfate, the solvent is removed under reduced pressure and the residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=2:1). This gives ethyl (1R,3S)-1-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]cyclopropanecarboxylate as a colorless oil. C25H33NO5 (427.55), MS (ESI): 428 (M+H+).

Workup

  1. additionare then added
  2. stirringthe mixture is stirred at room temperature for 90 min
  3. extractionextracted with methyl tert-butyl ether
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography on silica gel (n-heptane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2029a895678149a5bceefe9e6b7f0eda
Source dataset
uspto-grants-2011_01
Patent number
US07872034B2

Reaction notes

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