Diethyl Ether → HCID 178499986, compound

HRID 516896Notes

Reaction equation

HRID 516896 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.C[CH2:9][O:10]CC.[Si:13]([O:20][C:21]1[CH:48]=[CH:47][C:24]([CH2:25][C:26]2[C:27](=[O:46])[O:28][C:29](=[O:45])[C:30]=2[C@H:31]2[CH2:36][CH2:35][C@@H:34]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:33][CH2:32]2)=[CH:23][CH:22]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CO>[Si:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25]/[C:26](=[C:30](\[C@H:31]2[CH2:32][CH2:33][C@@H:34]([O:37][Si:38]([C:41]([CH3:42])([CH3:43])[CH3:44])([CH3:40])[CH3:39])[CH2:35][CH2:36]2)/[C:29]([O:10][CH3:9])=[O:45])/[C:27]([O:28][CH3:1])=[O:46])=[CH:47][CH:48]=1)([C:16]([CH3:18])([CH3:17])[CH3:19])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 178455041HCID 178455041, compound

Product 1

HCID 178499986HCID 178499986, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2.0 M trimethylsilyldiazomethane solution in ether (0.43 ml, 0.85 mmol) was added to a solution of 3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)furan-2,5-dione (60 mg, 0.11 mmol) in methanol (1.5 ml) at room temperature. The mixture was stirred at room temperature for 5 hr, and the solvent was removed by distillation under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=93:7) to give the title compound as a yellow oil (55 mg, yield 85%).

Workup

  1. customthe solvent was removed by distillation under reduced pressure
  2. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=93:7)

Sources & evidence

ORD record
ord-543f49b80c324985ba8488122e2386de
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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