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tert-Butyl methyl ether → Tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate

HRID 854671
Notes
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Reaction equation

HRID 854671 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.I[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27].[H-].[Na+].C(OC)(C)(C)C>CN(C)C=O>[CH3:18][C:10]([CH3:19])([CH2:9][CH2:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([O:1][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])[CH2:3]1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 219803112-(4-Methylphenyl)-4-iodomethyl-5-methyloxazoleHCID 69244301Tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate

Product 1

HCID 69244352Tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

365 mg of tert-butyl 4-(cis-3-hydroxycyclohexyl)-2,2-dimethylbutyrate are, together with 850 mg of 4-iodomethyl-5-methyl-2-(4 methylphenyl)oxazole, dissolved in 5 ml of dimethylformamide, and 110 mg of sodium hydride (60% strength in paraffin) are added. After 1 hour of stirring at room temperature, 100 ml of methyl tert-butyl ether are added and the reaction mixture is washed three times with water. The organic phase is dried over MgSO4 and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 330 mg of tert-butyl 2,2-dimethyl-4-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyl]butyrate as a white solid. C28H41NO4 (455.64), MS(ESI): 456 (M+H+).

Workup

  1. washthe reaction mixture is washed three times with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. customthe solvent is then removed under reduced pressure
  4. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-01f2fd27367148969257483291a1044d
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259177B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes